WO2018116073A1 - 1, 2, 3-thiadiazole compounds and their use as crop protecting agent - Google Patents

1, 2, 3-thiadiazole compounds and their use as crop protecting agent Download PDF

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Publication number
WO2018116073A1
WO2018116073A1 PCT/IB2017/057871 IB2017057871W WO2018116073A1 WO 2018116073 A1 WO2018116073 A1 WO 2018116073A1 IB 2017057871 W IB2017057871 W IB 2017057871W WO 2018116073 A1 WO2018116073 A1 WO 2018116073A1
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WO
WIPO (PCT)
Prior art keywords
thiadiazole
difluoromethyl
phenyl
carboxamide
carbothioamide
Prior art date
Application number
PCT/IB2017/057871
Other languages
French (fr)
Inventor
G. Renugadevi
Siva Kumar Reddy KOTLA
M. Sathishkumar
Dipankar Roy
Mohan Lal MEHTA
Sulur G MANJUNATHA
Ramdas Balu GADAKH
Suresh Kumar SUTHAR
Ruchi GARG
Mohan S.P. KUMAR
Rupesh Kumar Mishra
Santosh Shridhar AUTKAR
Hagalavadi M VENKATESHA
Alexander G. M. KLAUSENER
Konstantin POSCHARNY
Original Assignee
Pi Industries Ltd.
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Publication of WO2018116073A1 publication Critical patent/WO2018116073A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring

Definitions

  • the present invention relates to 1,2,3-thiadiazole compounds intended to protect crops by fighting against undesired phytopathogenic microorganisms. More precisely, the subject of the present invention relates to 1,2,3-thiadiazole carboxamide and thioamide compounds used to rotect crops by fighting against undesired phytopathogenic microorganisms.
  • W0199629871, WO2006098128 and WG2G10Q58830 discloses 1,2,3-thiadiazole carboxamide compounds and compositions containing these compounds for agricultural and horticultural crop disease control.
  • W0199854163 discloses a plant disease controlling agent containing 1,2,3- thiadiazole carboxamide compounds and a method for the use of these compounds.
  • JP 200G169461A discloses agricultural insecticidal and microbiocidal compounds composition comprising 1,2,3-thiadiazole carboxamide compounds.
  • JP2001139566 discloses pest control agent containing 1,2,3-thiadiazole carboxamide compounds and the method for using the same.
  • WO2000065914 discloses a fungicidal composition comprising 1 ,2,3-thiadiazole carboxamide compounds for seed treatment.
  • JP2001335570 discloses 1 ,2,3-thiadiazole carboxamide compounds for controlling insect pests, pathogenic fungi and weeds.
  • US 4,341,551 disclose 1,2,3 thiadiazole carboxylic acid derivatives as herbicide, fungicide and growth controlling agents.
  • WO2010037482 and WO2010089055 disclose use of sulfur-containing heterocyclic compounds for treating microbial and animal pathogens in plants of the family Musaceae.
  • CN106831647 disclosed 4-haioalkyl substituted 1,2,3 thiadiazole carboxamide derivative as insecticide.
  • a new family of compounds which possess the above mentioned effects or advantages.
  • a new family of compounds namely, 1, 2, 3-thiadiazole carboxamide or thioamide compounds wherein the substitution on thiadiazole and substitution on amine/aniline allow an unexpected and significantly higher activity against undesired microorganisms such as fungal or nematodes or bacterial pathogens.
  • This present invention relates to compounds of formula (I) and agronomically acceptable salts, metallic complexes, structural isomers, stereoisomers, diastereoisomers, enandomers, tautomers, or N- oxides thereof;
  • the present invention also relates to a composition
  • a composition comprising at least one compound of the present invention and at least one oilier active compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, nutrients and or mixtures thereof.
  • the present invention further relates to the use of the compound, the combination or the composition of the present invention and method of using the same, particularly in the field of agriculture mainly for protecting plants.
  • the compounds of the present invention are novel and have enhanced activity against phytopathogens.
  • the compounds of the present invention have application in the field of agriculture or horticultural crops.
  • the present invention relates to compounds of formula (I) and agronomically acceptable salts, metallic complexes, structural isomers, stereo-isomers, diastereoisomers, enantiomers tautomers, or N-oxides thereof;
  • R represents hydrogen, halogen, cyano, nitro, N(R ⁇ )(R ' ), Ci-Ce-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 - alkynyl, CrCe-haloaikyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, CrCe-alkoxy, CrC 6 - haloalkoxy, sulfanyl, pentafluoro-)>.
  • R 2 represents hydrogen, Ci-Ce-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, Cj-C6-alkoxy or C 3 -C 6 - cycloalkyl which may be substituted by R 7 ; or
  • T represents G, S, N(R 5 ), N(OR 5 ) or N-N(R 5 )(R 6 );
  • R 5 and R 6 may be same or different and is independently selected from hydrogen, Ci-Ce-alkyl, Ci-Ce-halogenoalkyl, Ci-Ce-alkoxy, Cj -Ce-halogenoalkoxy, Ci-Ce-alkoxy-CrCe-alkyl, C 2 -C 6 - alkenyl, C 2 -C 6 -halogenoalkenyl, C 2 -C 6 -al.kynyl, C 2 -C 6 -halogenoalkynyl, C 3 -C 6 -cycloalkyl, C 3 - Ce-cycloalkyi-CrCfi-alkyl, C 3 -C 6 -halogenocycloalkyl, formyl, CrC 6 -alkylcarbonyl, CrC 6 - halogenoalkylcarbonyl, Ci-Ce-alkylsulphonyi, C C 6 -halogenoalkylsulphony
  • R 7 is selected from the group consisting of halogen, cyano, riitro, amino, Ci-Ce-alkyl, Cj -Ce- halogenoalkyl, Q-Ce-alkoxy, CrCe-halogenoaikoxy, Ci-Ce-alkyicarbonyi, CrC 6 - halogenoalkylcarbonyl, Ci-Cg-alkoxycarbonyl, Cj -Ce-halogenoalkoxycarbonyl, C ⁇ -C - alkylaniinocarbonyl, Ci-Ce-di-alkyiaminocarbonyl, carboxyl, Ci-Ce-alkylsulfanyl, pentafluoro- > profession 6 -surfanyi, non aromatic-C 3 -C 6 -carbocycle, non aromatic-C 3 -C 6 -heterocycle; R " is selected from the group consisting of hydrogen, halogen, nitro, cyano,
  • R 8a epresents pentafluoro- ⁇ 6 - sulfanyl or pentafluoro ⁇ 0 -sulfajnyl-d-C 3 -al.kyl;
  • R 9 and R 10 may be the same or different represents hydrogen, cyano, Ci-C 6 -alkyl, d-C 6 - halogenoalkyl, d-C 6 -alkoxy, d-C 6 -halogenoalkoxy, d-C 6 -alkylcarbonyl, d-C 6 - aikoxycarbony!, d-C 6 -halogenoa!koxycarbonyl, Ci-C 6 -alkylaminocarbonyl, d-C 6 -di- alkylaminocarbonyl, d-d-alkylsulfanyl, C 3 -C 6 -carbocycle, CVd-heterocycle; or
  • R 9 and R l together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members 2
  • R la from d-C 6 - alkyl halides
  • R a , R a and R 4a selected from hydrogen, halogens, cyano, Nitro, d-C6-halogenated alky], CrC 6 -alkoxy, amino sulfonyl halides, d-C 6 -sulfoxide base, d-d-sulfone, Ci-d-alkyl sulfonamide, phenyl, 1 -5 same or different R "" substituted phenyl containing from 1 -3 same or different and selected from the oxygen atoms, nitrogen or sulfur atoms a 5-or-6- membered heterocyclic ring, 1-4 same or different R " ' substituted containing from 1-3 same or different and selected from the oxygen atoms and nitrogen atoms or sulfur atoms of 5-or 6-membered ring, with the proviso that the R a , R 3a and R 4a there can be only one hydrogen; R 3a selected from halogens, nitro, nitrile, Ci-Ce-alky
  • substitution R 1 of compound of general formula (I) is selected from halogen, halogenoaJkyl selected from -CHC1 2 , -C(R b )F 2 , -CHF 2 , -C(R b ) 2 -CF 3 , -CHF-CF 3 , -CF 2 - CF 3 ,-CHF-CF 2 -CF 3 , -CH 2 F, haloalkoxyalkyl selected from -C(R b ) 2 OCF 3 , -C(R b ) 2 OCHF 2 , - C(R b ) 2 OCH 2 F, -Ci-Cg-halogenoalkylsulfanyl-Ci-Ci-aikyl seicted from -C(R b ) 2 SCF 3 , - CH(R b )SCF 3 , -C(Rb) 2 SCHF 2 , -CH(R b ) 2
  • R b represents, hydrogen, halogen, CrCe-alkyl, Ci-Ce-haioalkyl; and other substitutions as defined in one of above embodiment.
  • R 1 is selected from halogen, halogenoalkyl selected from -CHC1 2 , -C(R b )F 2 , -CHF 2 , - C(R b ) 2 -CF 3 , -CHF-CF 3 , -CF 2 -CF 3 ,-CHF-CF 2 -CF 3 , -CH 2 F, haloalkoxyalkyl selected from - C(R b ) 2 OCF 3 , -C(R b ) 2 OCHF 2 , -C(R b ) 2 OCH 2 F, -C 1 -C8-halogenoaIkyIsulfanyI-C 1 -C 2 -alkyl seicted from -C(R b ) 2 SCF 3 , -CH(R b )SCF 3 , -C(R b ) 2 SCHF 2 , -CH(R b )SCHF 2 , Ci
  • substitution T of compound of general formula (I) is S.
  • preferred compound of general formula (I) are:
  • any of the compounds according to the invention can exist in one or more optical, geometric or chiral isomer forms depending on the number of asymmetric centres in the compound,
  • the invention thus relates equally to all the optical isomers and to their racemic or scalemic mixtures (the term "scalemic” denotes a mixture of enantiomers in different proportions), and to the mixtures of all the possible stereoisomers, in all proportions.
  • the diastereoisomers and/or the optical isomers can be separated according to the methods which are known per se by a person ordinary skilled in the art.
  • any of the compounds according to the invention can also exist in one or more geometric isomer forms depending on the number of double bonds in the compound.
  • the invention thus relates equally to ail geometric isomers and to all possible mixtures, in all proportions.
  • the geometric isomers can be separated according to general methods, which are known per se by a person ordinary skilled in the ait.
  • Any of the compounds according to the invention can also exist in one or more amorphic or isomorphic or polymorphic forms, depending on their preparation, purification storage and various other influencing factors.
  • the invention thus relates all the possible amorphic, isomorphic and polymorphic forms, in all proportions.
  • the amorphic, isomorphic and polymorphic forms can be prepared and/or separated and/or purified according to general methods, which are known per se by a person ordinary skilled in the art.
  • the terms “comprises”, “comprising”, “includes”, “including”, “has”, “having”, “contains”, “containing”, “characterized by” or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated.
  • a composition, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method.
  • the phrase “consisting of appears in a clause of the body of a claim, rather than immediately following the preamble it limits only the element set forth in that clause: other elements are not excluded from the claim as a whole.
  • transitional phrase “consisting essentially of” is used to define a composition or method that includes materials, steps, features, components or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components or elements do not materially affect the basic and novel characteristic(s) of the claimed invention.
  • the term “invertebrate pest” includes arthropods, gastropods and nematodes of economic importance as pests.
  • arthropod includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs and symphylans.
  • gastropod includes snails, slugs and other Stylommatophora.
  • nematode refers to a living organism of the Phylum Nematoda.
  • helminths includes roundworms, heartworms, phytophagous nematodes (Nematoda), flukes (Tematoda), acanthocephala and tapeworms (Cestoda).
  • invertebrate pest control means inhibition of invertebrate pest development (including mortality, feeding reduction, and/or mating disruption), and related expressions are defined analogously.
  • agronomic or “agriculturally” refers to the production of field crops such as for food and fiber and includes the growth of corn, soybeans and other legumes, rice, cereal (e.g., wheat, oats, barley, rye, rice, maize), leafy vegetables (e.g., lettuce, cabbage, and other cole crops), fruiting vegetables (e.g., tomatoes, pepper, eggplant, crucifers and cucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g., pome, stone and citrus), small fruit (berries, cherries) and other specialty crops (e.g., canola, sunflower, olives).
  • nonagronomic refers to other than field crops, such as horticultural crops (e.g., greenhouse, nursery or ornamental plants not grown in a field), residential, agricultural, commercial and industrial structures, turf (e.g., sod farm, pasture, golf course, lawn, sports field, etc.), wood products, stored product, agro-forestry and vegetation management, public health (i.e. human) and animal health (e.g., domesticated animals such as pets, livestock and poultry, undomesticated animals such as wildlife) applications.
  • horticultural crops e.g., greenhouse, nursery or ornamental plants not grown in a field
  • turf e.g., sod farm, pasture, golf course, lawn, sports field, etc.
  • wood products e.g., stored product, agro-forestry and vegetation management
  • public health i.e. human
  • animal health e.g., domesticated animals such as pets, livestock and poultry, undomesticated animals such as wildlife
  • Nonagronomic applications include protecting an animal from an invertebrate parasitic pest by administering a parasiticidally effeciive (i.e. biologically effective) amount of a compound of the present invention, typically in the form of a composition formulated for veterinary use, to the animal to be protected.
  • a parasiticidally effeciive i.e. biologically effective
  • the terms "parasiticidal” and “parasiticidally” refers to observable effects on an invertebrate parasite pest to provide protection of an animal from the pest. Parasiticidal effects typically relate to diminishing the occurrence or activity of the target invertebrate parasitic pest.
  • Such effects on the pest include necrosis, death, retarded growth, diminished mobility or lessened ability to remain on or in the host animal, reduced feeding and inhibition of reproduction. These effects on invertebrate parasite pests provide control (including prevention, reduction or elimination) of parasitic infestation or infection of the animal.
  • Compounds of the present disclosure may be present either in pure form or as mixtures of different possible isomeric forms such as stereoisomers or constitutional isomers.
  • the various stereoisomers include enantiomers, diastereomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, polymorphs, and geometric isomers. Any desired mixtures of these isomers fall within the scope of the claims of the present disclosure.
  • one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other isomer(s) or when separated from the other isomer(s). Additionally, the person skilled in the art knows processes or methods or technology to separate, enrich, and/or to selectively prepare said isomers. The meaning of various terms used in the description shall now be illustrated.
  • alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl” or - N(alkyl) or alkyicarbonyialkyl or alkylsuphonylamino includes straight -chain or branched Q to C 2 4 alkyl, preferably Cj to C 15 alkyl, more preferably C ⁇ to C 10 alkyl, most preferably Cj to C 6 alkyl.
  • alkyl include methyl, ethyl, propyl, 1-methyiethyl, butyl, 1 - methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3- methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyi, 1 ,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2- dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1- ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1 -e
  • the alkyl is at the end of a composite substituent, as, for example, in alkylcycloalkyl
  • the part of the composite substituent at the start for example the cycloalkyl
  • other radicals for example alkenyl, alkynyl, hydroxyl, halogen, carbonyl, carbonyloxy and the like, are at the end.
  • Alkenyl used either alone or in compound words includes straight-chain or branched Ci to C24 alkenes, preferably C ⁇ to C15 alkenes, more preferably C-, to C 10 alkenes, most preferably Ci to C 6 alkenes.
  • alkenes include ethenyl, 1 -propenyl, 2- propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1 -methyl- 1 -propenyl, 2-methyl-l- propenyl, l-methyl-2 -propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4- pentenyl, 1 -methyl- 1-butenyl, 2-metliyl- 1-butenyl, 3 -methyl- 1-butenyl, l-methyl-2-butenyl, 2- methyl-2-butenyl, 3-methyl-2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3- butenyl, l,l-dimethyl-2-propenyl, 1,2-dimethyl-l -propenyl, l,2-dimethyl-2-propen
  • Alkenyl also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. This definition also applies to alkenyl as a part of a composite substituent, for example haloalkenvl and the like, unless defined specifically elsewhere.
  • alkynes include ethynyl, 1 -propynyl, 2-propynyl, 1-butynyl, 2- butynyl, 3-butynyl, l-methyl-2 -propynyl, 1-pentynyl, 2-pentynyi, 3-pentynyl, 4-pentynyl, 1- methyl-2-butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-l-butynyl, 1 , l-dimethyi-2- propynyl, 1 -ethyl -2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1- methyl-2-pentynyl, l-methyl-3-pentynyl, l-methyl-4-pentynyl, 2
  • alkynyl can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. Cycloalkyl means alkyl closed to form a ring.
  • Representative examples include but are not limited to cyclopropyl, cyclopeiityi and cyclohexyl. This definition also applies to cycloalkyl as a part of a composite substituent, for example cycloalkylalkyl etc., unless specifically defined elsewhere.
  • Cycloalkenyl means alkenyl closed to form a ring including monocyclic, partially unsaturated hydrocarbyl groups. Representative examples include but are not limited to cyclopropenyl, cyclopentenyl and cyclohexenyl. This definition also applies to cycloalkenyl as a part of a composite substituent, for example cycloalkenyialkyl etc., unless specifically defined elsewhere.
  • Cycloalkynyl means alkynyl closed to form a ring including monocyclic, partially unsaturated groups. Representative examples include but are not limited to cyclopropynyl, cyclopentynyl and cyclohexynyl. This definition also applies to cycloalkynyl as a part of a composite substituent, for example cycloalkynylalkyl etc., unless specifically defined elsewhere.
  • Cycloalkoxy, cycloalkenyloxy and the like are defined analogously.
  • Non limiting examples of cycloalkoxy include cyclopropyioxy, cyclopentyloxy and cyclohexyloxy. This definition also applies to cycloalkoxy as a part of a composite substituent, for example cycloalkoxy alkyl etc., unless specifically defined elsewhere.
  • halogen either alone or in compound words such as “haioalkyl” or “halogenoalkyl”, includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haioalkyl” or “halogenoalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different.
  • haioalkyl examples include chloromethyl, bromomethyl, dichloromethyl, trichloromethyi, fluoromethyl, difluoromethyl, trifluoromethyi, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-irifluoroethyl, 2-chloro-2-fluoroethyl, 2- chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 1,1- dichl.oro-2,2,2-trifluoroethyl, and l,l ,l-trifluoroprop-2-yl. This definition also applies to hai
  • haloalkenyl or “halogenoalkenyl”, “haloalkynyl” or “halogenoalkynyl” are defined analogously except that, instead of alkyl groups, alkenyl and alkynyl groups are present as a part of the substituent.
  • haloalkoxy or "halogenoalkoy” means straight-chain or branched alkoxy groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above.
  • Non-limiting examples of haloalkoxy include chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1- bromoethoxy, 1 -fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroetlioxy, 2- chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2- trichloroethoxy,
  • haloalkylthio or "haloalkylsufanyl” or “halogenoalkylsulfanyl” means straight-chain or branched alkylthio groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above.
  • Non-limiting examples of haloalkylthio include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1- fluoroethylthio, 2- fluoroethylthio, 2,2-difiuoroethyithio, 2,2,2-tri.fluoroethylthio, 2-chloro-2- fluoroethylthio, 2- chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2 -trichloroet ylthio, pentafluoroethylthio and l
  • haloalkylsulfinyl examples include CF 3 S(G), CC1 3 S(G), CF 3 CH 2 S(G) and CF 3 CF 2 S(0).
  • haloalkylsulfonyl examples include CF 3 S(0) 2 , CC1 3 S(0) 2 , CF 3 CH 2 S(0) 2 and CF 3 CF 2 S(0) 2 .
  • Hydroxy means -OH
  • Amino means -N(R) 2 , wherein R can be H or any possible substituent such as alkyl
  • Carbonyl means -C(O)-
  • carbonyl oxy means -QC(Q) ⁇
  • sulfinyl means SO
  • sulfonyl means S(0) 2 .
  • alkoxy used either alone or in compound words included Cj to C 2 4 alkoxy, preferably Ci to Qs alkoxy, more preferably Ci to C 10 alkoxy, most preferably C. to C alkoxy.
  • alkoxy include methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1- methylpropoxy, 2-methylpropoxy, 1 , 1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2- methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1,1- dimethylpropoxy, 1 ,2-dimethylpropoxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, L l-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2- dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1 -et ylbutoxy,
  • Alkoxyalkyl denotes alkoxy substitution on alkyl.
  • alkoxyalkyl examples include CH3OCH2, CH3OCH 2 CH 2 , CH3CH 2 OCH 2 , CH3CH 2 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 . This definition also applies to alkoxyaikyi as a part of a composite substituent, for example haloalkoxyalkyl, unless specifically defined elsewhere.
  • alkoxyalkoxy denotes alkoxy substitution on alkoxy.
  • alkylthio includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, propylthio, 1 -methylethylthio, butylthio, 1-methylpropyithio, 2-methylpropylthio, 1, 1 - dimethyiethylthio, pentylthio, 1 -methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2- dimethylpropylthio, 1-ethylpropylthio, hexyithio, 1 , 1-diniethyl.propylthio, 1 ,2- dimethylpropylthio, 1 -methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4- methylpentylthio, 1 , 1 -dimethylbutylthio, 1 ,2-dimemylbutylthio, 1
  • Halogenocycloalkyi halogenocycloalkenyi, alkylcycloalkyl, cycloaikylalkyl, cycioalkoxyalkyl, alkylsuifinylalkyl, alkylsulfonylalkyl, halogenoalkylcarbonyl, cycloalkylcarbonyl, halogenoalkoxylalkyl, and the like, are defined analogously to the above examples.
  • alkyithioalkyl denotes alkylthio substitution on alky] .
  • Representative examples of “alkylthioalkyl” or “alkylsulfanylalkyl” include -CH 2 SCH 2 , -CH 2 SCH 2 CH 2 , CH 3 CH 2 SCH 2 , CH 3 CH 2 CH 2 CH 2 SCH 2 and CH 3 CH 2 SCH 2 CH 2 .
  • Alkylthioalkoxy denotes alkylthio substitution on alkoxy.
  • cycloalkylalkylamino denotes cycloalkyi substitution on aikyl amino. This definition also applies to alkoxy as a part of a composite substituent, for example haloalkoxy, alkenylaikoxy, alkynylalkoxy, etc., unless specifically defined elsewhere.
  • alkoxyalkoxyalkyl alkyiaminoalkyl, dialkylaminoalkyl, cycloalkylaminoalkyl, cycloalkylaminocarbonyi and the like, are defined analogously to "alkylthioalkyl” or cycloalkylalkylamino .
  • Al koxy carbonyl is an alkoxy group bonded to a skeleton via a carbonyl group (-CO- ). This definition also applies to alkoxycarbonyi as a part of a composite substituent, for example cycloalkylalkoxycarbonyl and the like, unless specifically defined elsewhere.
  • alkoxycarbonylalkylamino denotes alkoxy carbonyl substitution on alkyi amino.
  • Alkylcarbonylalkylamino denotes alkyi carbonyl substitution on alkyi amino.
  • alkylthioaikoxycarbonyl, cycloalkylalkylaminoalkyl and the like are defined analogously.
  • alkylsulfinyl include but are not limited to methylsulphinyl, ethylsulphinyl, propyisulphinyl, 1 -methylethylsulphinyL butyl sulphinyl, 1-methylpropylsulphinyl, 2- met ylpropylsulphinyl, 1 , 1 -dimethylethylsulphinyl, pentyl sulphinyl, 1 -methylbutylsulphinyl, 2- methylbutylsulphinyl, 3-methylbutylsuiphinyi, 2,2-dimethylpropyisulphinyl, 1- ethylpropylsulphinyl, hexylsuiphinyi, 1, 1-dimethylpropylsulphinyl, 1,2-dimethylpropylsulphinyl, 1-methylpentylsulphinyl, 2-methylpentylsulphinyl, 3-methyl
  • arylsulfmyl includes Ar- S(O), wherein Ar can be any carbocyle or heterocylcie. This definition also applies to alkylsulphinyl as a part of a composite substituent, for example haloaikyisulphiny! etc., unless specifically defined elsewhere.
  • alkylsulfonyl examples include but are not limited to methylsulphonyi, ethylsulphonyl, propyl sulphonyl, 1-methylethylsulphonyl, butylsulphonyl, 1 -methylpropylsulphonyl, 2- methylpropylsulphonyl, 1,1 -dimethylethylsulphonyl, pentylsulphonyl, l-methylbutyl sulphonyl,
  • arylsulfonyl includes Ar-S(0) 2 , wherein Ar can be any carbocyle or heterocylcie. This definition also applies to alkylsuiphonyl as a part of a composite substituent, for example alkylsulphonylalkyl etc., unless defined elsewhere.
  • Carbocycle includes "aromatic carbocyclic ring system” and “nonaromatic carbocylic ring system” or polycyclic or bicyeiic (spiro, fused, bridged, nonfused) ring compounds in which ring may be aromatic or non-aromatic (where aromatic indicates that the Huckel rule is satisfied and non-aromatic indicates that the Huckel rule is not statisfied).
  • hetero in connection with rings refers to a ring in which at least one ring atom is not carbon and which can contain 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs.
  • Heteroaryl means 5 or 6-membered, fully unsaturated monocyclic ring system containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur; if the ring contains more than one oxygen atom, they are not directly adjacent; 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom as ring members, for example (but not limited thereto) 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazoiyl, 5-isoxazoiyl, 3-isothiazolyi, 4-isofhiazoiyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl
  • 6-membered heteroaryl which contains one to four nitrogen atoms: 6-membered heteroaryl groups which, in addition to carbon atoms, may contain, respectively, one to three and one to four nitrogen atoms as ring members, for example (but not limited thereto) 2-pyridinyl, 3- pyridinyL 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyL 4-pyrimidinyl, 5-pyrimidinyL 2-pyrazinyl, l,3,5-triazin-2-yl, l,2,4-triazin-3-yl and 1,2,4, 5-tetrazin-3-yl; benzofused 5-membered heteroaryl containing one to three nitrogen atoms or one nitrogen atom and one oxygen or sulphur atom: for example (but not limited to) indol-l-yi, indol-2-yl, indol-3-yl, indol-4-yl, ind
  • lieterocycle means three- to fifteen-membered, preferably three- to tweleve-membered, saturated or unsaturated or partially unsaturated heterocycle containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur: mono, bi- or tricyclic heterocycles which contain, in addition to carbon ring members, one to three nitrogen atoms and/or one oxygen or sulphur atom or one or two oxygen and/or sulphur atoms; if the ring contains more than one oxygen atom, they are not directly adjacent; for example (but not limited to) oxiranyl, aziridinyl,
  • Trialkylsilyl includes 3 branched and/or straight-chain alkyl radicals attached to and linked through a silicon atom such as trimethylsilyl, triethylsilyl and t-butyl-dimeihylsilyl.
  • alotriaikyisilyl denotes at least one of the three alkyl radicals is partially or fully substituted with halogen atoms which may be the same or different
  • Alkoxytrialkylsilyl denotes at least one of the three alkyl radicals is substituted with one or more alkoxy radicals which may be the same or different
  • Trialkylsilyloxy denotes a trialkylsilyl moiety attached through oxygen.
  • alkylcarbonyl examples include C(0)CH 3 , C(0)CH 2 CH 2 Ce 3 and C(0)CH(CH 3 ) 2 .
  • the terni haloalkylsufonylaminocarbonyl, alkylsulfonylaminocarbonyl, alkylthioaikoxycarbonyl, alkoxycarbonyi alkyl amino and the like are defined analogously
  • Ci-C 3 alkylsulfonyl designates methyl sulfonyl through propylsulfonyl
  • C 2 alkoxyalkyl designates CH 3 OCH 2
  • C 3 alkoxyalkyl designates, for example, CH 3 CH(OCH 3 ), CH 3 OCH 2 CH 2 or CH 3 CH 2 OCH 2
  • C 4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH 3 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 .
  • the present invention also relates to a method for controlling unwanted microorganisms, wherein compounds of the formula (I) are applied to the microorganisms and/or in their habitat.
  • the present invention further provides a method for protecting seeds against unwanted microorganisms by using seed treated with at least one compound of the formula (I).
  • the compounds of the formula (I) can possess potent microbiocidal activity and can be used for the control of unwanted microorganisms, such as fungi, nematodes and bacteria, in crop protection and in the protection of such materials.
  • the compounds of the formula (I) can possess very good fungicidal properties and can be used in crop protection, for example for control of Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes .
  • the compounds of the formula (I) can be used as nematicides in crop protection, for example, for control of Rhabditida, Dorylaimida, and Tryplonchida.
  • the compounds of the formula (I) can be used as bactericides in crop protection, for example, for control of Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • the compounds of the formula (I) can be used as herbicides and can be effective against a broad spectrum of economically important mono- and dicotyledonous harmful plants.
  • Monocotyledonous broad-leaved weed species may include Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria and Cyperus species from the annual group and perennial species Agropyron, Cynodon, Imperata and Sorghum and also perennial Cyperus species.
  • Dicotyledonous broad-leaved weed species may include Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Sida, Matricaria and Abutilon on the annual side, and also Convolvulus, Cirsium, Rumex and Artemisia in the case of the perennial broad- leaved weeds. Harmful plants that occur in rice, such as, for example, Echinochloa, Sagittaria,
  • Alisma, Eieocharis, Scirpus and Cypems, can be controlled by the compounds of formula (I).
  • the compounds of the formula (I) can be used for curative or protective control of phytopathogenic fungi.
  • the invention therefore also relates to curative and protective methods for controlling phytopathogenic fungi by the use of the inventive active ingredients or compositions, which are applied to the seed, the plant or plant parts, the fruit or the soil in which the plants grow.
  • the compounds of the formula (I) can be used for controlling or preventing against phytopathogenic fungi, bacteria, insects, nematodes, mi es of agricultural crops and or horticultural crop s .
  • the compounds of the formula (I) can be used in crop protection, wherein the agricultural crops are cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbitaceae, oleaginous plants, tobacco, coffee, tea, cacao, sugar beet, sugar cane, cotton, potato, tomato, onions, peppers and other vegetables, and ornamentals.
  • the agricultural crops are cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbitaceae, oleaginous plants, tobacco, coffee, tea, cacao, sugar beet, sugar cane, cotton, potato, tomato, onions, peppers and other vegetables, and ornamentals.
  • a carrier is a natural or synthetic, organic or inorganic substance with which the active ingredients are mixed or combined for better applicability, in particular for application to plants or plant parts or seed.
  • the carrier which may be solid or liquid, are generally inert and should be suitable for use in agriculture.
  • Useful solid carriers include for example ammonium salts and natural rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic rock flours, such as finely divided silica, alumina and silicates; useful solid carriers for granules include: for example, crashed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and also synthetic granules of inorganic and organic flours, and granules of organic material such as paper, sawdust, coconut shells, maize cobs and tobacco stalks; useful emulsifiers and/or foam-formers include: for example nonionic and anionic emulsifiers, such as polyoxyethvlene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryi polyglycol ethers, alkylsulphonates, alkyl sulphates,
  • POE- and/or POP-polyol derivatives POE- and/or POP-sorbitan or -sugar adducts, alkyl or aryl sulphates, alkyl- or arylsulphonates and alkyl or aryl phosphates or the corresponding PO-ether adducts.
  • suitable are oligo- or polymers, for example those derived from vinylic monomers, from acrylic acid, from EO and/or PO alone or in combination with, for example, (poly) alcohols or (poly) amines. It is also possible to use lignin and its sulphonic acid derivatives, unmodified and modified celluloses, aromatic and/or aliphatic sulphonic acids and also their adducts with formaldehyde.
  • the active ingredients can be applied as such or converted to the customary formulations or in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, emulsions, water- or oil-based suspensions, powders, wettabie powders, pastes, soluble powders, soluble tablets, dusts, soluble granules, granules for broadcasting, suspoemulsion concentrates, natural products impregnated with active ingredient, synthetic substances impregnated with active ingredient, nutrients and also microencapsulations in polymeric substances.
  • Application is accomplished in a customary manner, for example by watering, spraying, atomizing, nursery boxes, broadcasting, dusting, foaming, spreading-on and the like. It is also possible to deploy the active ingredients by the ultra-low volume method or to inject the active ingredient preparation or the active ingredient itself into the soil. It is also possible to treat the seeds of the plants.
  • the active ingredients can be further converted to the nanoformulation with intent to further improve water solubility, thermal stability, bioavailability, sensory attributes, and physiological performance.
  • the formulations mentioned can be prepared in a manner known per se, for example by mixing the active ingredients with at least one customary extender, solvent or diluent, emulsifier, dispersant and/or binder or fixing agent, wetting agent, a water repellent, if appropriate siccatives and UV stabilizers and if appropriate dyes and pigments, antifoams, preservatives, secondary- thickeners, stickers, gibberellins and also other processing auxiliaries.
  • the present invention includes not only formulations which are already ready for use and can be deployed with a suitable apparatus to the plant or the seed, but also commercial concentrates which have to be diluted with water prior to use.
  • auxiliaries used may be those substances which are suitable for imparting particular properties to the composition itself and/or to preparations derived therefrom (for example spray liquors, seed dressings), such as certain technical properties and/or also particular biological properties.
  • Typical auxiliaries include extenders, solvents and carriers.
  • Suitable extenders are, for example, water, polar and nonpolar organic chemical liquids, for example from the classes of the aromatic and nonaromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which may optionally also be substituted, etherified and/or esterified), the ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly) ethers, the unsubstituted and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, the sulphones and sulphoxides (such as dimethyl sulphoxide).
  • Liquefied gaseous extenders or carriers are understood to mean liquids which are gaseous at standard temperature and under standard pressure, for example aerosol propellants such as halohydrocarbons, or else butane,
  • tackifiers such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
  • Further additives may be mineral, vegetable oils and methylated seed oils.
  • Useful liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, or else water.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
  • aliphatic hydrocarbons such as
  • compositions comprising compounds of the formula (I) may additionally comprise further components, for example surfactants.
  • surfactants are emulsifiers and/or foam formers, dispersants or wetting agents having ionic or nonionic properties, or mixtures of these surfactants.
  • Examples thereof are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic esters, taurine derivatives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty esters of polyois, and derivatives of the compounds containing sulphates, sulphonates and phosphates, for example alkylaryl poiyglycoi ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, protein hydrolysaies, lignosulphite waste liquors and methylcellulose.
  • the presence of a surfactant is necessary if one of the active ingredients and/or one of the
  • dyes such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Further additives may be perfumes, mineral or vegetable, optionally modified oils, waxes and nutrients (including trace nutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Additional components may be stabilizers, such as cold stabilizers, presen'atives, antioxidants, light stabilizers, or other agents which improve chemical and/or physical stability.
  • additional components may also be present, for example protective colloids, binders, adhesives, thickeners, thixotropic substances, penetrants, stabilizers, sequestering agents, complex formers.
  • the active ingredients can be combined with any solid or liquid additive commonly used for formulation purposes.
  • the formulations contain generally between 0.05 and 99% by weight, 0.01 and 98% by weight, preferably between 0.1 and 95% by weight, more preferably between 0.5 and 90% of active ingredient, most preferably between 10 and 70% by weight.
  • the formulations described above can be used for controlling unwanted microorganisms, in which the compositions comprising compounds of the formula (I) are applied to the microorganisms and/or in their habitat.
  • the present invention further relates to a composition for controlling unwanted microorganisms comprising at least one of the compounds of the formula (I) and one or more inert carrier.
  • the inert carrier further comprises agriculturally suitable auxiliaries, solvents, diluents, surfactants and/or extenders and the like.
  • the present invention further relates to a composition for controlling unwanted microorganisms, comprising at least one of the compounds of the formula (I) and/or one or more active compatible compounds selected from fungicides, bactericides, acaricides, insecticides, nemadcides, herbicides, biopesticides, plant growth regulators, antibiotics, nutrients and/or mixtures thereof.
  • the present invention further relates to a composition wherein the concentration of compounds having general formula (I) ranges from 1 to 90% by weight with respect to the total weight of the composition, preferably from 5 to 50% by weight with respect to the total weight of the composition.
  • the agrochemicai compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, more preferably between 1 and 70%, and in particular between 10 and 60%, by weight of active substance.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • solutions for seed treatment (IS), Suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (OS), water- dispersible powders for slurry treatment (WS), water- soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels (GF) are usually employed.
  • compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready-touse preparations.
  • Application can be carried out before or during sowing.
  • Methods for applying compound I and compositions thereof, respectively, onto plant propagation material, especially seeds include dressing, coating, pelleting, dusting, and soaking as well as in-furrow application methods.
  • compound I or the compositions thereof, respectively are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
  • the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2kg per ha, more preferably from 0.05 to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.
  • amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 40 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required.
  • the amount of active substance applied depends on the kind of application area and on the desired effect.
  • Amounts WO 2017/081312 PCT/EP2016/077524 customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1kg, of active substance per cubic meter of treated material.
  • Compounds of the formula (I) according to this invention, as well as salts, N-oxides, metal complexes, stereoisomers or polymorphs can be used as such or in formulations thereof and can be mixed with known mixing partners in order to broaden, for example, the activity spectrum or to prevent development of resistance.
  • Useful mixing partners include, for example, known fungicides, insecticides, acaiicides, nematicides, biopesticides and bactericides.
  • Ail named mixing partners of the classes (A) to (O) as described below can, if their functional groups enable this, optionally form salts with suitable bases or acids, appear as stereoisomers, even if not specifically mentioned in each case, or as polymorphs. They are also understood as being included herein.
  • A) Inhibitors of the ergo sterol biosynthesis for example (A01) aldimorph, (A02) azaconazole, (A03) bitertanol, (A04) bromuconazole, (AOS) cyproconazole, (A06) diclobutrazole, (A07) difenoconazole, (AOS) diniconazole, (A09) diniconazole-M, (A 10) dodemorph, (Al l) dodemorph acetate, (A12) epoxiconazole, (A13) etaconazole, (A14) fenarimol, (A 15) fenbuconazole, (A16) fenhexamid, (A17) fenpropidin, (A18) fenpropimorph, (A19) fluquinconazole, (A20) flurprimidol, (A21) flusilazole, (A01) al
  • B) Inhibitors of the respiratory chain at complex I or II for example (B01) bixafen, (B02) boscalid, (B03) carboxin, (B04) cypropamide, (BOS) diflumetorim, (B06) fenfuram, (B07) fluopyram, (B08) flutolanil, (B09) fluxapvroxad, (B IO) furametpyr, (B l l) turmecyclox, (B 12) isopyrazam (mixture of syn-epimeric racemate 1RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR), (B13) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), (B 14) isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (B15) isopyrazam (anti-epimeric enantiomer 1S
  • D) Inhibitors of the mitosis and cell division for example (DOT) benomyl, (D02) carbendazim, (D03) chlorfenazole, (D04) diethofencarb, (D05) ethaboxam, (D06) fluopicolide, (D07) fiiberidazole, (DOS) pencycuron, (D09) thiabendazole, (D1.0) thiophanate-methyl, (Dl l) thiophanate, (D12) zoxamide, (D13) 5-chloro-7-(4-methylpiperidin- l-yl)-6-(2,4,6- trifluorophenyl)[l,2,4]triazol.o l ,5-aJpyrimidine, (D14) 3-chloro-5-(6-chloropyridin-3-yl)-6- methyl-4-(2,4,6- trifluorophenyl) pyridazine.
  • F Compounds capable to induce a host defence, for example (F01) acibenzolar-S-methyl, (F02) isotianil, (F03) probenazole, (F04) tiadinil, (F05) laminarin.
  • G Inhibitors of the amino acid and/or protein biosynthesis, for example (G01) andoprim, (G02) blasticidin-S, (G03) cyprodinil, (G04) kasugamycin, (G05) kasugamycin hydrochloride hydrate, (G06) mepanipyrim, (G07) pyrimethanil, (G08) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4- dihydroisoquinolin-l-yl)quinoline, (G09)oxytetracycline,(G10)streptomycin.
  • G01 andoprim
  • G02 blasticidin-S
  • G03 cyprodinil
  • G04 kasugamycin
  • G05 kasugamycin hydrochloride hydrate
  • G06 mepanipyrim
  • G07 pyrimethanil
  • G08 3-(5-fluoro-3,3,4,4-tetramethyl-3,4- dihydroisoquinol
  • H Inhibitors of the ATP production, for example (HOI) fentin acetate, (H02) fentin chloride, (H03) fentinhydroxide, (H04) silthiofam.
  • Inhibitors of the cell wall synthesis for example (101) benthiavalicarb, (102) dimethomorph, (103) flumorph, (104) iprovalicarb, (105) mandipropamid, (106) polyoxins, (107) polyoxorim, (108) vaiidamycin A, (109) valifenaiate, (110) polyoxin B, (11 1) (2E)-3-(4-tert- butylphenyl)-3-(2-chIoropyri.din-4-yl)-l -(morpholin-4-yI)prop-2-en-l-one, (112) (2Z)-3-(4-tert- butylphenyl)-3-(2-chloropyridii -4-yl)-l-(morpholin-4-yl)prop-2-en-l-one.
  • J) Inhibitors of the lipid and membrane synthesis for example (J01) biphenyl, (J02) chloroneb, (J03) dicloran, (.104) edifenphos, (J05) etridiazole, (J06) iodocarb, (.107) iprobenfos, (J08) isoprothiolane, (J09) propamocarb, (J 10) propamocarb hydrochloride, (Jl l) prothiocarb, (J12) pyrazophos, (J13) quintozene, (.114) tecnazene, (J 15) toclofos-methyl.
  • K) Inhibitors of the melanin biosynthesis for example (K01 ) carpropamid, (K02) diclocymet, (K03) fenoxanil, (K04) phthalide, (K05) pyroquilon, (K06) tolprocarb, (K07)tricyclazole.
  • L) Inhibitors of the nucleic acid synthesis for example (L01) benalaxyl, (L02) benalaxyl-M (kiralaxyl), (L03) bupirimate, (L04) clozylacon, (LOS) dimethirimol, (L06) ethirimol, (L07) furalaxyl, (L08) hymexazol, (L09) metalaxyl, (L10) metalaxyl-M (mefenoxam), (Ll l) ofurace, (L12) oxadixyl, (L13) oxoiinic acid, (L1.4)octhilinone.
  • Inhibitors of the nucleic acid synthesis for example (L01) benalaxyl, (L02) benalaxyl-M (kiralaxyl), (L03) bupirimate, (L04) clozylacon, (LOS)
  • M Inhibitors of the signal transduction, for example (M01 ) chlozolinate, (M02) fenpiclonil, (M03) fludioxonil, (M04) iprodione, (M05) procymidone, (M06) quinoxyfen, (M07) vinclozolin, (M08) proquinazid.
  • the compound of formula (I) can be mixed with one or more active compatible compound selected from insecticides/acaricides/neniaticides class, which are specified herein by their common names that are known and described, for example in The Pesticide Manual 17 th Ed., or can be searched in the internet (e.g. under www.alanwood.net/pesticides).
  • Acetylcholinesterase (AChE) inhibitors such as carbamates, for example alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxira, butoxycarboxim, carbaryl, carbofuran, carbosuifan, ethiofencarb, fenobucarb. forrnetanate, f rathiocarb, isoprocarb, metliiocarb.
  • AChE Acetylcholinesterase
  • GABA-gated chloride channel antagonists such as cyclodiene organodiioriiies, for example chlordaiie and endosulfan or pbenvlpvrazoles (fiproles), for example ethiproie and fiproni!.
  • Sodium channel modulators/voltage-dependent sodium channel blockers such as pyretfcroids, for example acrinathrin, allethrin, d-cis-trans allethrin, d- trans allethrin, bifenthrin, bioal!ethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfl.uih.rin, bela-cyfl.uih.rin, eyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypem ethrin, beta- c yperi nethrin , theta-c y ermeihrin, zeia-cypermeihrin , eyphenofhrin [( 1R )-t
  • Nicotinic acetylcholine receptor (rs.ACbR) competitive modulators such as neonicotinoids, for example acetamiprid, elothiaiiidin, dinotefuran, imidacloprid, niteiipyram, thiacloprid and iliia.mer.liox am or nicotine or sulfoxaflor or Oupyradi urone.
  • neonicotinoids for example acetamiprid, elothiaiiidin, dinotefuran, imidacloprid, niteiipyram, thiacloprid and iliia.mer.liox am or nicotine or sulfoxaflor or Oupyradi urone.
  • Nicotinic acetylcholine receptor (nACliR) allosteric modulators such as spinosyns, for example spinetoram and spiiiosad.
  • Glutamate-gaied chloride channel (GluCl) allosteric modulators such as avennectins / milbemycins, for example abamectin, emamectin benzoate, lepimeciin and milbemectin,
  • Juvenile hormone mimics such as juvenile hormone analogues, for example hydroprene, kinoprene and meth prene or fenoxycarb or pyriproxyfen.
  • Active compounds with unknown or non-specific mechanisms of action such as alkyl halides for example as methyl bromide and other alkyl halides or chloropicrin or fluorides or borates or tartar emetic or methyl isocyanate generators.
  • Chordotonai organ TRPV channel modulators such as pyridine azomethine derivatives, for example pyme rozine and pyrifluquinazon or flonicamid,
  • Mite growth inhibitors for example clofentezine, hexylhiazox and diflovidazin or etoxazole.
  • Microbial disrupters of insect gut midgut for example Bacillus thuringiensis subspecies israelensis. Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki. Bacillus thuringiensis subspecies tenehrionis and Bacillus sphaericus and BT crop proteins: CrylAb, CrvlAc, CrvlFa, CrylA 105, Cry2Ab, Vip3a, mCrySA, Cry3Ab, Cry3Bb, Cry34Abl / Cry35Abl.
  • Inhibitors of mitochondrial ATP synthase such as organodn miticides, for example azocyelotin, cyhexatin and fenbutatin oxide or diafentliiuron or propargite or tetradifon.
  • organodn miticides for example azocyelotin, cyhexatin and fenbutatin oxide or diafentliiuron or propargite or tetradifon.
  • Nicotinic acetylcholine receptor (iiAChR) channel blockers such as bensultap, eartap- hydrochloride, thiocyclam and thiosultap-sodium,
  • Inhibitors of chit i biosynthesis, type 0, such as bistrifluoron, chlorfluazuron. difhibenzuron, fliicycioxiiron, fiufenoxuron, hexaflumuron, !ufenuron, novahiron, novifiumuron, teflubenzuroii and triflumuroii.
  • Inhibitors of chitin biosynthesis type 1. such as buprofezin,
  • Molting disrupters (particularly in Dipteran), such as cyromazine
  • Ecclysone receptor agonists such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide.
  • Octopamine receptor agonists such as amitraz.
  • Mitochondrial complex III electron transport inhibitors such as hydramethyinon or acequinocyl or fluacrypyrim or bifenazate.
  • (23) inhibitors of acetyl CoA carboxylase such as tetronic and tetramic acid derivatives, for example spirodiclofen, spiromesifen and spirotetramat.
  • Mitochondrial complex IV electron transport Inhibitors such as phosphides, for example aluminum phosphide, calcium phosphide, zinc phosphide and phosphlne or cyanides.
  • Mitochondrial complex II electron transport Inhibitors such as heta-ketonilrlle derivatives, for example cyeiiopyrafen and eyflumetofen or carboxanilides.
  • afidopyropen afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, chinomethionat, cryolite, cycianillprole, eyeloxaprid, cyhalodiamide, dicloromezodaz, dieofol, dlflovidazin, flometoquin, fi uazaindolizine, lluensulibiie, flufeiierim, ilufenoxystrobin, flufiprole, fluhexafon, fluopyram, fluralaner, fluxametamide, fufenozide.
  • guadipyr heptafiuthrin, irnldac otliiz, iprodlone, lotilaner, meperfluthriii, paichongdiiig, pyflubumide, pyridaly , pyrifhiquinazon, pyriminostrobin, sarolaner, tetramethylftuthrin, tetraniliprole, tetrachlorantraniliprole, tioxazafeii, trifluraezopyrim and iodomethane; iiirthermore, preparations based on Bacillus firtnus (1-1582, BioNeem, Votivo), and the following known active compounds: l- ⁇ 2-fluoiO ⁇ 4 ⁇ meihyI-5-[(2,2,2 ⁇
  • the compounds of formula (I) may be used to treat several fungal pathogens.
  • pathogens of fungal diseases which can be treated in accordance with the invention include: diseases caused by powdery mildew pathogens, for example Blumeria species, for example
  • Podosphaera species for example Podosphaera leucotricha
  • Sphaerotheca species for example Sphaerotheca fuliginea
  • Uncinuia species for example Uncinuia necator
  • Erysiphe species for example Erysiphe dehor ac earn:
  • Gymnosporangium species for example Gymnosporangium sabinae
  • Hemileia species for example Hemileia vastatrix
  • Phakopsora species for example Phakopsora pachyrhizi or Phakopsora meihomiae
  • Puccinia species for example Puccinia recondita, Puccinia graminis oder Puccinia striiformis
  • Uromyces species for example Uromyces appendiculatus ;
  • Albugo species for example Albugo Candida
  • Bremia species for example Bremia lactucae
  • Peronospora species for example Peronospora pisi or P. brassicae
  • Phytophthora species for example Phytophthora infestans
  • Plasmopara species for example Plasmopara viticola
  • Pseudoperonospora species for example Pseudoperonospora humuli or Pseudoperonospora cubensis
  • Pythium species for example Pythium ultimum
  • Pythium species for example Pythium ultimum
  • leaf blotch diseases and leaf wilt diseases caused, for example, by Aiiernaria species, for example Alternaria solani; Cercospora species, for example Cercospora beticola; Cladiosporium species, for example Cladiosporium, cucumerinum,; Cochliobolus species, for example Cochliobolus sativus (conidial form: Drechslera, syn: Helminthosporium) or Cochliobolus miyabeanus; Colletoirichum species, for example Colletoirichum lindemuthanium; Cycloconium species, for example Cycloconium oleaginum; Diaporthe species, for example Diaporthe citri Elsinoe species, for example Elsinoe fawcettii; Gloeosporium species, for example Gloeosporium laeticolor; Glomerella species, for example Glomerella cingulata; Guignardia species, for example Guignard
  • Mycosphaerella species for example Mycosphaerella graminicola, Mycosphaerella arachidicola or Mycosphaerella fijiensis
  • Phaeosphaeria species for example Phaeosphaeria nodoruni
  • Pyrenophora species for example Pyrenophora teres or Pyrenophora tritici repenlis
  • Ramularia species for example Ramularia collo-cygni or Ramularia areola: Rhynchosporium species, for example Rhynchosporium secalis; Septoria species, for example Septoria apii or Septoria lycopersici; Stagonospora species, for example Stagonospora nodorum; Typhula species, for example Typhula incarnata; Venturia species, for example Venturia inaequalis;
  • Corticium species for example Corticium graminearum
  • Fusarium species for example Fusarium oxysporum
  • Gaeumannomyces species for example Gae niannomyces graminis
  • Plasmodiophora species for example Plasmodiophora brassicae
  • Rhizoctonia species for example Rhizoctonia solani
  • Sarocladium species for example Sarocladium oryzae
  • Sclerotium species for example Sclerotium oryzae
  • Tapesia species for example Tapesia acuformis
  • Thielaviopsis species for example Thielaviopsis basicola
  • Ganoderrna species for example Ganoderrna lucidum
  • Thielaviopsis species for example Thielaviopsis basicola
  • Ganoderrna species for example Ganoderrna lucidum
  • ear and panicle diseases caused, for example, by Alternaria species, for example Alternaria spp.; Aspergillus species, for example Aspergillus flavus; Cladosporium species, for example Cladosporium cladosporioides; Claviceps species, for example Claviceps purpurea; Fusarium species, for example Fusarium culmorum; Gibberella species, for example Gibberella zeae; Monographella species, for example Monographella nivalis; Stagnospora species, for example Stagnospora nodorum;
  • Sphacelotheca species for example Sphacelotheca reiliana
  • Tilletia species for example Tilletia caries or Tilletia controversa
  • Urocystis species for example Urocystis occulta
  • Ustilago species for example Uslilago nuda
  • Alternaria species for example Alternaria brassicicola
  • Aphanomyces species for example Aphanomyces euteiches
  • Ascochyta species for example Ascochyta lends
  • Aspergillus species for example Aspergillus flavus
  • Cladosporium species for example Cladosporium herbarum
  • Cochliobolus species for example Cochliobolus sativus (conidial form: Drechslera, Bipolaris Syn: Helminthosporium); Colletotrichurn species, for example Colletotrichum coccodes
  • Fusarium species for example Fusarium culmorum Gibberella species, for example Gibberella zeae
  • Macrophomina species for example Macrophomina phaseolina
  • Microdochiurn species for example Microdochiurn nivale: Monographella species,
  • Nectria species for example Nectria galligena:
  • wilt diseases caused, for example, by MonUinia species, for example Monilinia laxa;
  • Exobasidium species for example Exobasidium vexans
  • Taphrina species for example Taphrina deformans
  • degenerative diseases in woody plants caused, for example, by Esca species, for example Phaeomoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranea; Ganoderma species, for example Ganoderma boninense;
  • Botrytis species for example Botrytis cinerea
  • Rhizoctonia species for example Rhizoctonia solani
  • Helminthosporium species for example Helminthosporium solani
  • diseases caused by bacterial pathogens for example Xanthomonas species, for example Xanthomonas carnpestris pv. oryzae; Pseudomonas species, for example Pseudomonas syringae /; ⁇ ! . lachrymans; Erwinia species, for example Erwinia amylovora Ralstonia species, for example Ralstonia solanacearum;
  • phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophora gregatd), pythium rot (Pythium aphaniderrnaium, Pythiurn irregulare, Pythium deharyanum, Pythium myrioiyium, Pythium ultimuni), rhizoctonia root rot, stem decay, and damping-off (Rhizoctonia solani), sclerotinia stem decay (Sclerotinia sclerotiorum), sclerotinia southern blight (Sclerotinia roljsii), thielaviopsis root rot (Thielaviopsis basicola).
  • the invention also relates to a method of controlling damage to plant and parts thereof by plant parasitic nematodes (Endoparasitic, Semiendoparasitic and Ectoparasitic nematodes), especially plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne arenaria and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Glohodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes,
  • Plants which can be treated in accordance with the invention include the following: Rosaceae sp (for example pome fruits such as apples, pears, apricots, cherries, almonds and peaches), Rihesioidae sp.,
  • Juglandaceae sp. Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp.,
  • Actinidaceae sp. Lauraceae sp., Musaceae sp. (for example banana trees and plantations),
  • Rubiaceae sp. for example coffee
  • Theaceae sp., Sterculiceae sp., Rutaceae sp. for example lemons, oranges and grapefruit
  • Vitaceae sp. for example grapes
  • Solanaceae sp. for example tomatoes, peppers
  • Liliaceae sp. for example lettuce
  • Umbelliferae sp., Cr ciferae sp. Chenopodiaceae sp.
  • Cucurbitaceae sp. for example cucumber
  • Alliaceae sp. for example leek, onion
  • Papilionaceae sp. for example peas
  • major crop plants such as PoaceaeiGramineae sp. (for example maize, turf, cereals such as wheat, rye, rice, barley, oats, millet and triticale),
  • Asteraceae sp. for example sunflower
  • Brassicaceae sp. for example white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, and oilseed rape, mustard, horseradish and cress
  • Fabacae sp. for example bean, peanuts
  • Papilionaceae sp. for example soya bean
  • Solanaceae sp. for example potatoes
  • Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plan cultivars which are protectable and non-protectable by plant breeders' rights.
  • Plant parts are understood to mean all parts and organs of plants above and below the ground, such as shoot, leaf, flower and root, examples of which include leaves, needles, stalks, stems, flowers, fruit bodies, fruits and seeds, and also roots, tubers and rhizomes.
  • the plant parts also include harvested material and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, slips and seeds.
  • the invention furthermore includes a method for treating seed, particularly seeds (dormant, primed, pregerminated or even with emerged roots and leaves) treated with at least one of the compounds of the formula (I) and compositions thereof.
  • inventive seeds are used in methods for protection of seeds and emerged plants from the seeds from phytopathogenic harmful fungi. In these methods, seed treated with at least one inventive active ingredient is used.
  • the present invention therefore also relates to a method for protecting seeds, germinating plants and emerged seedlings against attack by animal pests, nematodes and/or phytopathogenic harmful microorganisms by treating the seeds with an inventive composition.
  • the invention also relates to the use of the compositions according to the invention for treating seeds for protecting the seeds, the germinating plants and emerged seedlings against animal pests and/or phytopathogenic microorganisms.
  • the invention further relates to seeds which have been treated with an inventive composition for protection from animal pests and/or phytopathogenic microorganisms ,
  • One of the advantages of the present invention is that the treatment of the seeds with these compositions not only protects the seed itself, but also the resulting plants after emergence, from animal pests and/or phytopathogenic harmful microorganisms. In this way, the immediate treatment of the crop at the time of sowing or shortly thereafter protect plants as well as seed treatment in prior to sowing. It is likewise considered to be advantageous that the inventive active ingredients or compositions can be used especially also for transgenic seed, in which case the plant which grows from this seed is capable of expressing a protein which acts against pests, herbicidal damage or abiotic stress. The treatment of such seeds with the inventive active ingredients or compositions, for example an insecticidal protein, can result in control of certain pests.
  • the compounds of the formula (I) are suitable for protection of seed of any plant variety which is used in agriculture, in the greenhouse, in forests or in horticulture. More particularly, the seed is that of cereals (such as wheat, barley, rye, millet and oats), oilseed rape, maize, cotton, soybeen, rice, potatoes, sunflower, beans, coffee, beet (e.g. sugar beet and fodder beet), peanut, vegetables (such as tomato, cucumber, onions and lettuce), lawns and ornamental plants. Of particulai- significance is the treatment of the seed of wheat, soybean, oilseed rape, maize and rice.
  • transgenic seed As also described below, the treatment of transgenic seed with the inventive active ingredients or compositions is of particular significance.
  • This refers to the seed of plants containing at least one heterologous gene which allows the expression of a polypeptide or protein, e.g. having insecticidal properties.
  • heterologous genes in transgenic seeds may originate, for example, from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavihacter, Glomus or Gliodadium.
  • These heterologous genes preferably originate from Bacillus sp., in which case the gene product is effective against the European corn borer and/or the Western com rootworm.
  • the heterologous genes originate from Bacillus thuringiensis .
  • the inventive composition is applied to seeds either alone or in a suitable formulation.
  • the seed is treated in a state in which it is sufficiently stable for no damage to occur in the course of treatment.
  • seeds can be treated at any time between harvest and some time after sowing. It is customary to use seed which has been separated from the plant and freed from cobs, shells, stalks, coats, hairs or the flesh of the fruits. For example, it is possible to use seed which has been harvested, cleaned and dried down to a moisture content of less than 15% by weight.
  • seed which, after drying, for example, has been treated with water and then dried again or seeds just after priming, or seeds stored in primed conditions or pre-germinated seeds, or seeds sown on nursery trays, tapes or paper.
  • the amount of the inventive composition applied to the seed and/or the amount of further additives is selected such that the germination of the seed is not impaired, or that the resulting plant is not damaged. This must be ensured particularly in the case of active ingredients which can exhibit phvtotoxic effects at certain application rates.
  • the compounds of the formula (I) can be applied directly, i.e. without containing any other components and without having been diluted. In general, it is preferable to apply the compositions to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art.
  • the compounds of the formula (I) can be converted to the customary formulations relevant to on-seed applications, such as solutions, emulsions, suspensions, powders, foams, slurries or combined with other coating compositions for seed, such as film forming materials, pelleting materials, fine iron or other metal powders, granules, coating material for inactivated seeds, and also ULV formulations.
  • seeds can be coated with polymer.
  • the polymer coating is comprised of a binder, a wax and a pigment, and one or more stabilizers in an amount effective to stabilize the suspension.
  • the binder can be a polymer selected from the group consisting of vinyl acetate-ethylene copolymer, vinyl acetate homopolymer, vinyl acetate-acrylic copolymer, vinylacrylic, acrylic, ethylene-vinyl chloride, vinyl ether maleic anhydride, or butadiene styrene. Other similar polymers can be used.
  • formulations are prepared in a known manner, by mixing the active ingredients or active ingredient combinations with customary additives, for example customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, adhesives, gibberellins, and also water.
  • customary additives for example customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, adhesives, gibberellins, and also water.
  • Useful dyes which may be present in the seed dressing formulations usable in accordance with the invention are all dyes which are customary for such purposes. It is possible to use either pigments, which are sparingly soluble in water, or dyes, which are soluble in water. Examples include the dyes known by the names Rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red I.
  • Useful wetting agents which may be present in the seed dressing formulations usable in accordance with the invention are all substances which promote wetting and which are conventionally used for the formulation of active agrochemical ingredients.
  • Usable with preference are alkylnaphthaienesuiphonates, such as diisopropyl- or diisobutylnaphthalenesulphonates.
  • Useful dispersants and/or emulsifiers which may be present in the seed dressing formulations usable in accordance with the invention are all nonionic, anionic and cationic dispersants conventionally used for the formulation of active agrochemical ingredients. Usable with preference are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
  • Useful nonionic dispersants include especially ethylene oxide/propylene oxide block polymers, alkylphenol poiygiycol ethers and tristryrylphenol polyglycol ether, and the phosphated or sulphated derivatives thereof.
  • Suitable anionic dispersants are especially lignosulphonates, polyacrylic acid salts and arylsulphonate/formaldehyde condensates.
  • Antifoams which may be present in the seed dressing formulations usable in accordance with the invention are all foam-inhibiting substances conventionally used for the formulation of active agrochemical ingredients. Silicone antifoams and magnesium stearate can be used with preference.
  • Preservatives which may be present in the seed dressing formulations usable in accordance with the invention are all substances usable for such purposes in agrochemical compositions. Examples include dichiorophene and benzyl alcohol hemiformal.
  • Secondary thickeners which may be present in the seed dressing formulations usable in accordance with the invention are all substances usable for such purposes in agrochemical compositions.
  • Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
  • Adhesives which may be present in the seed dressing formulations usable in accordance with the invention are all customary binders usable in seed dressing products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.
  • the formulations for on-seed applications usable in accordance with the invention can be used to treat a wide variety of different kinds of seed either directly or after prior dilution with water.
  • the concentrates or the preparations obtainable therefrom by dilution with water can be used to dress the seed of cereals, such as wheat, barley, rye, oats, and triticale, and also seeds of maize, soybean, rice, oilseed rape, peas, beans, cotton, sunflowers, and beets, or else a wide variety of different vegetable seeds.
  • the formulations usable in accordance with the invention, or the dilute preparations thereof, can also be used for seeds of transgenic plants. In this case, additional effects may also occur in interaction with the substances formed by expression.
  • the application rate of the formulations usable in accordance with the invention can be varied within a relatively wide range. It is guided by the particular content of the active ingredients in the formulations and by the seeds.
  • the application rates of each single active ingredient are generally between 0.001 and 15 g per kilogram of seed, preferably between 0.01 and 5 g per kilogram of seed.
  • the application rates can be varied within a relatively wide range, depending on the kind of application.
  • the application rate of the inventive active ingredients is: in the case of treatment of plant parts, for example leaves: from 0.1 to 10000 g ha, preferably from 10 to 1000 g/ha, more preferably from 30 to 300 g/ha (in the case of application by watering or dripping, it is even possible to reduce the application rate, especially when inert substrates such as rockwool or perlite are used); in the case of seed treatment: from 0.1 to 10 kg per 100 kg of seed, preferably from 1 to 150 g per 100 kg of seed, more preferably from 2.5 to 25 g per 100 kg of seed, even more preferably from 2.5 to 12.5 g per 100 kg of seed; in the case of soil treatment: from 0.1 to 10000 g/ha, preferably from 1 to 5000 g/ha.
  • the compounds of the formula (I) can, at particular concentrations or application rates, also be used as herbicides, safeners, growth regulators or agents to improve plant properties, or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including compositions against yiroids) or as compositions against MLO (Mycoplasma-like organisms) and RLO (Rickettsia- like organisms).
  • Plant growth regulators may exert various effects on plants. The effect of the substances depends essentially on the time of application in relation to the developmental stage of the plant, the plant variety and also on the amounts of active ingredient applied to the plants or their environment and on the type of application. In each case, growth regulators should have a particular desired effect on the crop plants.
  • Growth regulating effects comprise earlier germination, better emergence, more developed root system and/or improved root growth, increased ability of tillering, more productive tillers, earlier flowering, increased plant height and/or biomass, shorting of stems, improvements in shoot growth, number of kernels/ear, number of ears/m 2 , number of stolons and/or number of flowers, enhanced harvest index, bigger leaves, less dead basal leaves, improved phyliotaxy, earlier maturation/ earlier fruit finish, homogenous riping, increased duration of grain filling, better fruit finish, bigger fruit/vegetable size, sprouting resistance and reduced lodging.
  • Increased or improved yield is referring to total biomass per hectare, yield per hectare, kernel/fruit weight, seed size and/or hectolitre weight as well, as to improved product quality, comprising:
  • improved marketability relating to improved fruit/grain quality, size distribution (kernel, fruit, etc.), increased storage/shelf-life, firmness /softness, taste (aroma, texture, etc.), grade (size, shape, number of berries, etc.), number of berries/fruits per bunch, crispness, freshness, coverage with wax, frequency of physiological disorders, colour, etc.:
  • Plant growth-regulating compounds can be used, for example, to slow down the vegetative growth of the plants.
  • Such growth depression is of economic interest, for example, in the case of grasses, since it is thus possible to reduce the frequency of grass cutting in ornamental gardens, parks and sport facilities, on roadsides, at airports or in fruit crops.
  • Also of significance is the inhibition of the growth of herbaceous and woody plants on roadsides and in the vicinity of pipelines or overhead cables, or quite generally in areas where vigorous plant growth is unwanted.
  • growth regulators for inhibition of the longitudinal growth of cereal. This reduces or completely eliminates the risk of lodging of the plants prior to harvest.
  • growth regulators in the case of cereals can strengthen the culm, which also counteracts lodging.
  • the employment of growth regulators for shortening and strengthening culms allows the deployment of higher fertilizer volumes to increase the yield, without any risk of lodging of the cereal crop.
  • vegetative growth depression allows denser planting, and it is thus possible to achieve higher yields based on the soil surface.
  • Another advantage of the smaller plants obtained in this way is that the crop is easier to cultivate and harvest.
  • Reduction of the vegetative plant growth may also lead to increased or improved yields because the nutrients and assimilates are of more benefi to flower and fruit formation than to the vegetative parts of the plants.
  • growth regulators can also be used to promote vegetative growth. This is of great benefit when harvesting the vegetative plant parts. However, promoting vegetative growth may also promote generative growth in that more assimilates are formed, resulting in more or larger fruits,
  • beneficial effects on growth or yield can be achieved through improved nutrient use efficiency, especially nitrogen (N)-use efficiency, phosphours (P)-use efficiency, water use efficiency, improved transpiration, respiration and/or C0 2 assimilation rate, better nodulation, improved Ca-metabolism etc.
  • nitrogen (N)-use efficiency especially nitrogen (N)-use efficiency, phosphours (P)-use efficiency, water use efficiency, improved transpiration, respiration and/or C0 2 assimilation rate, better nodulation, improved Ca-metabolism etc.
  • growth regulators can be used to alter the composition of the plants, which in turn may result in an improvement in quality of the harvested products. Under the influence of growth regulators, parthenocarpic fruits may be formed. In addition, it is possible to influence the sex of the flowers. It is also possible to produce sterile pollen, which is of great importance in the breeding and production of hybrid seed. Use of growth regulators can control the branching of the plants. On the one hand, by breaking apical dominance, it is possible to promote the development of side shoots, which may be highly desirable particularly in the cultivation of ornamental plants, also in combination with an inhibition of growth. On the other hand, however, it is also possible to inhibit the growth of the side shoots. This effect is of particular interest, for example, in the cultivation of tobacco or in the cultivation of tomatoes.
  • the amount of leaves on the plants can be controlled such that defoliation of the plants is achieved at a desired time.
  • defoliation plays a major role in the mechanical harvesting of cotton, but is also of interest for facilitating harvesting in other crops, for example in viticulture.
  • Defoliation of the plants can also be undertaken to lower the transpiration of the plants before they are transplanted.
  • growth regulators can modulate plant senescence, which may result in prolonged green leaf area duration, a longer grain filling phase, improved yield quality, etc. Growth regulators can likewise be used to regulate fruit dehiscence. On the one hand, it is possible to prevent premature fruit dehiscence. On the other hand, it is also possible to promote fruit dehiscence or even flower abortion to achieve a desired mass ("thinning"). In addition, it is possible to use growth regulators at the time of harvest to reduce the forces required to detach the fruits, in order to allow mechanical harvesting or to facilitate manual harvesting. Growth regulators can also be used to achieve faster or else delayed ripening of the harvested material before or after harvest. This is paiticulai y advantageous as it allows optimal adjustment to the requirements of the market.
  • growth regulators in some cases can improve the fruit colour.
  • growth regulators can also be used to synchronize maturation within a certain period of time. This establishes the prerequisites for complete mechanical or manual harvesting in a single operation, for example in the case of tobacco, tomatoes or coffee.
  • growth regulators By using growth regulators, it is additionally possible to influence the resting of seed or buds of the plants, such that plants such as pineapple or ornamental plants in nurseries, for example, germinate, sprout or flower at a time when they are normally not inclined to do so. in areas where there is a risk of frost, it may be desirable to delay budding or germination of seeds with the aid of growth regulators, in order to avoid damage resulting from late frosts.
  • growth regulators can induce resistance of the plants to frost, drought or high salinity of the soil. This allows the cultivation of plants in regions which are normally unsuitable for this purpose.
  • the compounds of the formula (I) also exhibit a potent strengthening effect in plants. Accordingly, they can be used for mobilizing the defences of the plant against attack by undesirable microorganisms.
  • Plant- strengthening (resistance-inducing) substances in the present context are substances capable of stimulating the defence system of plants in such a way that the treated plants, when subsequently inoculated with undesirable microorganisms, develop a high degree of resistance to these microorganisms.
  • plant physiology effects comprise the following: Abiotic stress tolerance, comprising tolerance to high or low temperatures, drought tolerance and recovery after drought stress, water use efficiency (correlating to reduced water consumption), flood tolerance, ozone stress and UV tolerance, tolerance towards chemicals like heavy metals, salts, pesticides etc.
  • Biotic stress tolerance comprising increased fungal resistance and increased resistance against nematodes, viruses and bacteria.
  • biotic stress tolerance preferably comprises increased fungal resistance and increased resistance against nematodes.
  • Increased plant vigor comprising plant health / plant quality and seed vigor, reduced stand failure, improved appearance, increased recovery after periods of stress, improved pigmentation (e.g. chlorophyll content, stay-green effects, etc.) and improved hoto synthetic efficiency.
  • the compounds of the formula (I) can reduce the mycotoxin content in the harvested material and the foods and feeds prepared therefrom.
  • Mycotoxins include particulai y, but not exclusively, the following: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2- and HT2-toxin, fumonisins, zearalenon, moniliformin, fusarin, diaceotoxyscirpenol (DAS), beauvericin, enniatin, fusaroproliferin, fusarenol, ochratoxins, patulin, ergot alkaloids and aflatoxins which can be produced, for example, by the following fungi: Fusarium spec, such as F.
  • verticillioides etc. and also by Aspergillus spec, such as A. flavus, A, parasiticus, A. nomius, A. ochraceus, A. clavatus, A. terreus, A. versicolor, Penicillium spec, such as P. verrucosum, P. viridicatum, P. citrinum, P. expansum, P. claviforme, P. roqueforti, Claviceps spec, such as C. purpurea, C. fusiformis, C. paspali, C. africana, Stachybotrys spec and others.
  • Aspergillus spec such as A. flavus, A, parasiticus, A. nomius, A. ochraceus, A. clavatus, A. terreus, A. versicolor, Penicillium spec, such as P. verrucosum, P. viridicatum, P. citrinum, P
  • the compounds of the formula (I) can also be used in the protection of materials, for protection of industrial materials against attack and destruction by phytopathogenic fungi.
  • the compounds of the formula (I) can be used as antifouling compositions, alone or in combinations with other active ingredients.
  • Industrial materials in the present context are understood to mean inanimate materials which have been prepared for use in industry.
  • industrial materials which are to be protected by- inventive compositions from microbial alteration or destruction may be adhesives, glues, paper, wallpaper and board/cardboard, textiles, carpets, leather, wood, fibers and tissues, paints and plastic articles, cooling lubricants and other materials which can be infected with or destroyed by microorganisms.
  • Parts of production plants and buildings for example cooling-water circuits, cooling and heating systems and ventilation and air-conditioning units, which may be impaired by the proliferation of microorganisms may also be mentioned within the scope of the materials to be protected.
  • Industrial materials within the scope of the present invention preferably include adhesives, sizes, paper and card, leather, wood, paints, cooling lubricants and heat transfer fluids, more preferably wood.
  • the compounds of the formula (I) may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.
  • the compounds of the formula (I) may also be used against fungal diseases liable to grow on or inside timber.
  • the term "timber" means all types of species of wood, and all types of working of this wood intended for construction, for example solid wood, high-density wood, laminated wood, and plywood.
  • the method for treating timber according to the invention mainly consists in contacting a composition according to the invention; this includes for example direct application, spraying, dipping, injection or any other suitable means.
  • the compounds of the formula (I) can be used to protect objects which come into contact with saltwater or brackish water, especially hulls, screens, nets, buildings, moorings and signalling systems, from fouling.
  • the compounds of the formula (I) can also be employed for protecting storage goods.
  • Storage goods are understood to mean natural substances of vegetable or animal origin or processed products thereof which are of natural origin, and for which long-term protection is desired.
  • Storage goods of vegetable origin for example plants or plant parts, such as stems, leaves, tubers, seeds, fruits, grains, can be protected freshly harvested or after processing by (pre)drying, moistening, comminuting, grinding, pressing or roasting.
  • Storage goods also include timber, both unprocessed, such as construction timber, electricity poles and barriers, or in the form of finished products, such as furniture.
  • Storage goods of animal origin are, for example, hides, leather, furs and hairs.
  • the inventive compositions may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.
  • Microorganisms capable of degrading or altering the industrial materials include, for example, bacteria, fungi, yeasts, algae and slime organisms.
  • the compounds of the formula (I) preferably act against fungi, especially moulds, wood-discoloring and wood-destroying fungi (Ascomycetes,
  • Examples include microorganisms of the following genera: Altemaria, such as Alternaria tenuis: Aspergillus, such as Aspergillus niger; Chaetomium, such as Chaetomium globosum; Coniophora, such as Coniophora puetana; Lentinus, such as Lentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporus, such as Polyporus versicolor, Aureobasidium, such as Aureobasidium pullulans; Sclerophoma, such as Sclerophoma pityophila Trichoderma, such as Trichoderma viride Qphiostoma spp., Ceratocystis spp., Humicola spp., Peiriella spp., Trichurus spp., Co
  • the compounds of the formula (I) also have very good antimycotic effects. They have a very broad antimycotic activity spectrum, especially against dermatophytes and yeasts, moulds and diphasic fungi (for example against Candida species, such as Candida albicans, Candida glahraia), and Epidermophyion floccosurn, Aspergillus species, such as Aspergillus niger and Aspergillus fumigatus, T ' richophyton species, such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii.
  • the enumeration of these fungi by no means constitutes a restriction of the mycotic spectrum covered, and is merely of illustrative character.
  • the compounds can be used also to control important fungal pathogens in fish and Crustacea farming, e.g. saprolegnia diclina in trouts, saprolegnia parasitica in crayfish.
  • the compounds of the formula (I) can therefore be used both in medical and in non-medical applications.
  • the compounds of the formula (I) can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules.
  • Application is accomplished in a customary manner, for example by watering, spraying, atomizing, broadcasting, dusting, foaming, spreading-on and the like. It is also possible to deploy the active ingredients by the ultra-low volume method or to inject the active ingredient preparation/the active ingredient itself into the soil. It is also possible to treat the seed of the plants.
  • plants and their parts in accordance with the invention, preferably with wild plant species and plant cultivars, or those obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and also parts thereof.
  • transgenic plants and plant cultivars obtained by genetic engineering methods if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • the terms "parts” or “parts of plants” or “plant parts” have been explained above. More preferably, plants of the plant cultivars which are commercially available or are in use are treated in accordance with the invention.
  • Plant cultivars are understood to mean plants which have new properties ("traits") and have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be cultivars, varieties, bio- or genotypes.
  • the method of treatment according to the invention can be used in the treatment of genetically modified organisms (GMQs), e.g. plants or seeds.
  • Genetically modified plants are plants of which a heterologous gene has been stably integrated into genome.
  • the expression "heterologous gene” essentially means a gene which is provided or assembled outside the plant and when introduced in the nuclear, chloroplastic or mitochondrial genome gives the transformed plant new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by downregulating or silencing other gene(s) which are present in the plant (using for example, antisense technology, cosuppression technology, RNA interference - RNAi - technology or microRNA - miRNA - technology).
  • a heterologous gene that is located in the genome is also called a transgene.
  • a transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.
  • Plants and plant cultivars which are preferably to be treated according to the invention include all plants which have genetic material which impart particularly advantageous, useful traits to these plants (whether obtained by breeding and/or biotechnological means). Plants and plant cultivars which are also preferably to be treated according to the invention are resistant against one or more biotic stresses, i.e. said plants show a better defense against animal and microbial pests, such as against nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and/or viroids. Plants and plant cultivars which may also be treated according to the invention are those plants which are resistan to one or more abiotic stresses.
  • Abiotic stress conditions may include, for example, drought, cold temperature exposure, heat exposure, osmotic stress, flooding, increased soil salinity, increased mineral exposure, ozone exposure, high light exposure, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients, shade avoidance.
  • Plants and plant cultivars which may also be treated according to the invention are those plants characterized by enhanced yield characteristics. Increased yield in said plants can be the result of, for example, improved plant physiology, growth and development, such as water use efficiency, water retention efficiency, improved nitrogen use, enhanced carbon assimilation, improved photosynthesis, increased germination efficiency and accelerated maturation.
  • Yield can furthermore be affected by improved plant architecture (under stress and non- stress conditions), including but not limited to, early flowering, flowering control for hybrid seed production, seedling vigor, plant size, internode number and distance, root growth, seed size, fruit size, pod size, pod or ear number, seed number per pod or ear, seed mass, enhanced seed filling, reduced seed dispersal, reduced pod dehiscence and lodging resistance.
  • Further yield traits include seed composition, such as carbohydrate content and composition for example cotton or starch, protein content, oil content and composition, nutritional value, reduction in anti -nutritional compounds, improved processabiiity and better storage stability. Plants that may be treated according to the invention are hybrid plants that already express the characteristic of heterosis or hybrid vigor which results in generally higher yield, vigor, health and resistance towards biotic and abiotic stresses).
  • Plants or plant cultivars which may be treated according to the invention are herbicide-tolerant plants, i.e. plants made tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation, or by selection of plants containing a mutation imparting such herbicide tolerance.
  • Plants or plant cultivars which may also be treated according to the invention are insect-resistant transgenic plants, i.e. plants made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such insect resistance.
  • Plants or plant cultivars obtained by plant biotechnology methods such as genetic engineering which may also be treated according to the invention are tolerant to abiotic stresses. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such stress resistance.
  • Plants or plant cultivars obtained by plant biotechnology methods such as genetic engineering which may also be treated according to the invention show altered quantity, quality and/or storage- stability of the harvested product and/or altered properties of specific ingredients of the harvested product.
  • Plants or plant cultivars which may also be treated according to the invention are plants, such as cotton plants, with altered fiber characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered fiber characteristics.
  • Plants or plant cultivars which may also be treated according to the invention are plants, such as oilseed rape or related Brassica plants, with altered oil profile characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered oil profile characteristics.
  • Plants or plant cultivars which may also be treated according to the invention are plants, such as oilseed rape or related Brassica plants, with altered seed shattering characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered seed shattering characteristics and include plants such as oilseed rape plants with delayed or reduced seed shattering. Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as tobacco plants, with altered post-translational protein modification patterns.
  • a compound of formula (5) is prepared as per the procedure reported in Med. Chem. Research, 22, 1747-1755 (2013).
  • a compound of formula (1) is reacted with compound of general formula (2) to get a compound of formula (3).
  • the compound (3) is cyelized to get a 1 ,2,3-thiadiazole derivative of formula (4).
  • the derivative (4) is hydrolysed to get a compound of formula (5).
  • the compound (5) is halogenated to get the acid chloride of formula (6),
  • the acid halide of formula (6) is reacted with an amine of the general formula (7) to get the compound of formula (8).
  • the acid of formula (5) is reacted with an amine of the general formula (7) using in the presence of suitable condensing agent to get the compound of formula (8).
  • the acid of formula (4) is reacted with an amine of the general formula (7) using in the presence of suitable condensing agent to get the compound of formula (8).
  • the amide of formula (8) is treated with suitable thionating agent to give thioamide of formula (9).
  • N-substituted formula of (7) can be prepared by known processes such as reductive animation of aldehydes or ketones (Bioorganics and Medicinal Chemistry Letters 16 (2006) 2013-2016 or reduction of imines (Tetrahedron, 61 (49), 11521-1 1764, 2005), or nucleophilc substitution of a halogen (journal of Medicinal chemistry 45 (18), 3878-3890, 2002)
  • Step A Benzyl (Z)-2-(4-ethoxy-l,l-difluoro-4-oxobutan-2-ylidene)hydrazine-l-carboxylate
  • Step D Preparation of 4-(difluoromethyl)-N-(3-(trifluoromethoxy)phenyl)-l, 2, 3- thiadiazole-5-carboxamide
  • Step-A Ethyl (Z)-2 ⁇ (4-ethoxy ⁇ l,i,l-trifluoro-4 ⁇ oxobistan ⁇ 2 ⁇ ylidene)hydrazine ⁇ l- carboxylate
  • Step-B Ethyl 4-(trifluoromethyl)-l, 2, 3-thiadiazoIe-5 ⁇ carfooxyIate
  • Step-C Preparation of N-(4-(pentafluoro- 6-sulfanyl)phenyl)-4-(trifluoromethyl)-l,2,3- thiadiazole-5-carboxamide
  • Step A 4-(difluoromethyl)-N-(4-(pentafluoro- 6-sulfanyl)phenyl)-l, 2, 3-tfaiadiazoIe- ⁇ - carboxamide
  • Step A N-(4-bromo-2-(trifluoromethyl)phenyl)-4-(difluoromethyl)-l, 2, 3-thiadiazole-5- carboxamide
  • Step B N-(4-bromo-2-(trifluoromethyl)phenyl)-4-(difluoromethyl)-N-methyl-l,2,3- thiadiazole-5-carboxamide
  • Step A 4-(difluoromethyl)-N-(3-((trifluoromethyl)thio)phenyl)-l,2,3-thiadiazole-5- carboxamide
  • Step B N-(2-Chloro-4(trifluoromethyl)sulfinyl)phenyl)-4-(difluoromethyl)-l,2,3- thiadiazole-5-carboxamide
  • Step B N-(2-Bromo-4(trifluoromethyl)thio)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carboxamide
  • Step A 3-(isopropylthio)aniline.
  • Step B 4-(difluoromethyl)-N-(3-(isopropylthio)phenyl)-l,2,3-thiadiazole-5-carboxamide
  • Step D N-(3-(N-cyanopropan-2-ylsulfonimidoyl)phenyl)-4-(difluoromethyl)-l, 2, 3- thiadiazole-5-carboxamide.
  • M+l means the molecular ion peak, plus or minus 1 a.m.u. (atomic mass unit) respectively, as observed in mass spectroscopy l H-NMR data of selected examples are written in form of ⁇ -NMR-peak lists. To each signal peak are listed the 6- value in ppm and the no of proton in round brackets.

Abstract

24859-P4PCT ABSTRACT 1, 2, 3-Thiadiazole compounds and their use as crop protecting agent The present invention relates to 1,2,3-thiadiazole compounds of the formula (I), wherein R1, R2, T and Z have the meanings as defined in description. The invention further relates to their use to protect crops by fighting against undesired phytopathogenic microorganisms.

Description

f ,2,3~THIAMAZOLE COMPOUNDS AND THEIR USE AS CROP PROTECTING
The present invention relates to 1,2,3-thiadiazole compounds intended to protect crops by fighting against undesired phytopathogenic microorganisms. More precisely, the subject of the present invention relates to 1,2,3-thiadiazole carboxamide and thioamide compounds used to rotect crops by fighting against undesired phytopathogenic microorganisms.
Figure imgf000002_0001
The control of damages to crops caused by phytopathogenic microorganisms is extremely important in achieving high crop efficiency. For instance, plant disease damage to ornamental, vegetable, field crops, cereal, and fruit crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. Many products are commercially available to control such damages. The need continues for new compounds which are more effective, less costly, less toxic, and environmentally safer and/or have different modes of action. Certain 1 ,2,3- thiadiazol carboxamide derivatives are disclosed in literature as microbiocidal active ingredients in pesticides.
W0199629871, WO2006098128 and WG2G10Q58830 discloses 1,2,3-thiadiazole carboxamide compounds and compositions containing these compounds for agricultural and horticultural crop disease control. W0199854163 discloses a plant disease controlling agent containing 1,2,3- thiadiazole carboxamide compounds and a method for the use of these compounds. JP 200G169461A discloses agricultural insecticidal and microbiocidal compounds composition comprising 1,2,3-thiadiazole carboxamide compounds. JP2001139566 discloses pest control agent containing 1,2,3-thiadiazole carboxamide compounds and the method for using the same. WO2000065914 discloses a fungicidal composition comprising 1 ,2,3-thiadiazole carboxamide compounds for seed treatment. JP2001335570 discloses 1 ,2,3-thiadiazole carboxamide compounds for controlling insect pests, pathogenic fungi and weeds. US 4,341,551 disclose 1,2,3 thiadiazole carboxylic acid derivatives as herbicide, fungicide and growth controlling agents. WO2010037482 and WO2010089055 disclose use of sulfur-containing heterocyclic compounds for treating microbial and animal pathogens in plants of the family Musaceae.
CN106831647 disclosed 4-haioalkyl substituted 1,2,3 thiadiazole carboxamide derivative as insecticide.
The effectiveness of the thiadiazole carboxamide derivatives described in the prior art is good, but leaves something to be desired in various cases. Therefore, it is always of high interest in agriculture to use novel pesticidal compounds in order to avoid and/or control the development of microorganisms such as fungal or bacterial pathogens or pests being resistant to known active ingredients. It is therefore of high interest to use novel compounds being more active than those already known, with the aim of decreasing the amounts of active compound to be used, whilst at the same time maintaining an effectiveness at least equivalent to the already known compounds.
We have now found a new family of compounds which possess the above mentioned effects or advantages. A new family of compounds namely, 1, 2, 3-thiadiazole carboxamide or thioamide compounds wherein the substitution on thiadiazole and substitution on amine/aniline allow an unexpected and significantly higher activity against undesired microorganisms such as fungal or nematodes or bacterial pathogens.
SUMMARY OF THE INVENTION
This present invention relates to compounds of formula (I) and agronomically acceptable salts, metallic complexes, structural isomers, stereoisomers, diastereoisomers, enandomers, tautomers, or N- oxides thereof;
Figure imgf000003_0001
wherein the substituents of R' , R", T and Z are as defined in the description.
The present invention also relates to a composition comprising at least one compound of the present invention and at least one oilier active compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, nutrients and or mixtures thereof. The present invention further relates to the use of the compound, the combination or the composition of the present invention and method of using the same, particularly in the field of agriculture mainly for protecting plants. The compounds of the present invention are novel and have enhanced activity against phytopathogens. The compounds of the present invention have application in the field of agriculture or horticultural crops.
DETAILED DESCRIPTION OF THE INVENTION
Accordingly, the present invention relates to compounds of formula (I) and agronomically acceptable salts, metallic complexes, structural isomers, stereo-isomers, diastereoisomers, enantiomers tautomers, or N-oxides thereof;
Figure imgf000004_0001
wherein,
1 ^ A
R represents hydrogen, halogen, cyano, nitro, N(R~)(R '), Ci-Ce-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, CrCe-haloaikyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, CrCe-alkoxy, CrC6- haloalkoxy, sulfanyl, pentafluoro-)>.6-sulfanyl, pentafluoro- 6-sulfariyl-C1-C6-alkyl, CrC6- alky 1 sulfanyl, Ci-Ce-halogenoalkyl sulfanyl, (VCe-alkyisulfmyl, Ci-Ce-halogenoalkylsuIfinyl, CrCe-alkylsulfonyl, CrCe-halogenoalkylsulfonyl, Cj-Ce-alkylsulfonyloxy, C5-C10- arylsulfonyloxy, C3-C6-carbocycle, C3-C6-heterocycle, each of these groups may be optionally substituted by halogen, cyano, Ci-Ce-alkyl, Ci-Ce-haloaikyl, carboxyl, Q-Ce-alkylcarbonyl, Cr C6-halogenoalkylcarbonyl;
R2 represents hydrogen, Ci-Ce-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cj-C6-alkoxy or C3-C6- cycloalkyl which may be substituted by R7; or
R and R" together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(-S), S(0)m and Si(R may form a five to eight ing, which for its part may be substituted ne or more of R 7
membered r by o ; Z is selected from the group consisting of Q-Ce-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein one or more carbon atoms may be replaced by heteroatoms selected from N, O and S or fused and/or nonfused C3-C12-carbocycle or fused and/or nonfused C3-C12-heterocycl.e, wherein one or more heteroatoms is selected from N, O and S, and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)m and Si(R ')2, eac of these groups may be optionally substituted by one or more groups of R8 or R8aor both;
T represents G, S, N(R5), N(OR5) or N-N(R5)(R6); R" and R may be same or different and is independently selected from hydrogen, Cr-Ce.-alkyl, C2-C6-alkenyl, C2-C6-alkyn l, Ci-Ce-alkylcarbonyl, C2-C6-aIkenylcarbonyl, C2-C6- alkynylcarbonyl, Ci-Ce-aikylsulphonyl, CrCe-alkylsulfonyloxy, Cs-Cio-arylsuifonyloxy, C=0(- NR'iRy), wherein R and Ry may be same or different and is independently selected from hydrogen or CrC6-alkyl; R and K* may be optionally substituted by one or more groups of R ; or
R3 and R4 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)m and Si(R )2, may form a three to seven membered ring, which for its part may be substituted by one or more substituents independently selected from halogen, cyano, Cj -Ce-alkyl, C]-C6-haloalkyl, carboxyl, CrC6- alkylcarbonyl, Q-Ce-halogenoalkylcarbonyl;
R5 and R6 may be same or different and is independently selected from hydrogen, Ci-Ce-alkyl, Ci-Ce-halogenoalkyl, Ci-Ce-alkoxy, Cj -Ce-halogenoalkoxy, Ci-Ce-alkoxy-CrCe-alkyl, C2-C6- alkenyl, C2-C6-halogenoalkenyl, C2-C6-al.kynyl, C2-C6-halogenoalkynyl, C3-C6-cycloalkyl, C3- Ce-cycloalkyi-CrCfi-alkyl, C3-C6-halogenocycloalkyl, formyl, CrC6-alkylcarbonyl, CrC6- halogenoalkylcarbonyl, Ci-Ce-alkylsulphonyi, C C6-halogenoalkylsulphonyl, phenyl, naphthyl or phenylmethylene wherein R5 and R6 may be optionally substituted by one or more groups of R7;
R7 is selected from the group consisting of halogen, cyano, riitro, amino, Ci-Ce-alkyl, Cj -Ce- halogenoalkyl, Q-Ce-alkoxy, CrCe-halogenoaikoxy, Ci-Ce-alkyicarbonyi, CrC6- halogenoalkylcarbonyl, Ci-Cg-alkoxycarbonyl, Cj -Ce-halogenoalkoxycarbonyl, C\-C - alkylaniinocarbonyl, Ci-Ce-di-alkyiaminocarbonyl, carboxyl, Ci-Ce-alkylsulfanyl, pentafluoro- >„6-surfanyi, non aromatic-C3-C6-carbocycle, non aromatic-C3-C6-heterocycle; R " is selected from the group consisting of hydrogen, halogen, nitro, cyano, -N(RJ)(R X hydroxy!, carboxyl, sulfanyl, amidine, -S(0)„(R9)=N-R10, -N=S(0)„(R9)(R10), pentafluoro-λ6- sulfanyl, pentafluoro- 6-sulfanyl-C1-C6-alkyl, Ci-C6-alkyl, Ci-Ce-halogenoalkyl, Ci-Ce-alkenyl, Ci-Ce-halogenoalkenyl, C2-C6-alkynyl, Ci-Ce-halogenoalkynyl, CrC6-alkoxy, CrC6- halogenoalkoxy, C2-C6-alkenyloxy, C2-C6-halogenoalkenyloxy, C2-C6-alkynyloxy, C2-C6- halogenoalkynyloxy, d- s-alkoxy-Ci-Ce-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-d-C6-alkyl, C3-C6-halogenocycloalkyl, Ci-Ce-alkoxycarbonyl, Ci-Ce-alkylamino, d-Ce-alkoximino-d-Ce- alkyl, d -Ce-alkylsulfanyl, d-Ce-halogenoalkylsulfanyl, Cr-Ce-alkylsu!finyl, d -C6- halogenoalkylsulfinyl, d-C6-alkylsulfonyl, d-C6-halogenoalkyl-sulfonyl, formy!, formyloxy, formylamino, carbamoyl, N-hydroxycarbamoyl, carbamate, (hydroxyimino)-C1-C6-alkyl, d-C6- alkylcarbonyl, Cj -Ce-haiogenoalkylcarbonyl, d-C6-alkylcarbamoyl, Cj -Ce-di-alkylcarbamoyl, Ci-Ce-alkyloxycarbamoyl, Ci-Ce-alkoxycarbamoyl, N-Ci-Ce-alkyl-alkoxycarbamoyl-d-Ce- alkoxycarbonyl, C¾ -Ce-haiogenoalkoxycarbonyi, Ci-Ce-alkylaminocarbonyl, d -C6-di- alkylaminocarbonyl, CrC6-alkylcarbonyloxy, CrC6-halogenoalkylcarbonyloxy, d-C6- alkylcarbonylamino, CrCe-halogenoalkylcarbonylamino, d-C6-alkylaminocarbonyloxy, d-C6- di-alkylaiTiinocarbonyloxy, CrC6-alkyloxycarbonyloxy, CrC6-alkoxyimino, d-C6-(d-C6- alkoxyimino)-aikyl, C1-C6-(C2-C6-alkenyloxyimino)-alkyl, d-Ce-id-Ce-alkynyloxyimirio)- alky!, (benzyloxyimino^d-Ce-alkyl, d-C6-tri(alkyi)silyl, d-C6-tri(alkyi)silyl-d-C6-alkyl, C3- Ce-carbocycle, C3-C6-heterocycle, Cs-do-aryloxy, Cs-Cio-heteroaryloxy, CVdo-aryl sulfanyl, Cs-Cio-arylamino, naphthyl, Cs-do-arylmethylene and each of these groups may be optionally substituted by one or more groups of R7; or
2 8 o S
R and R or tw R together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)m and Si(R2)2, may form a five to eight membered ring, which for its part may be substituted by one or more of R ;
R8a epresents pentafluoro-λ6- sulfanyl or pentafluoro^0-sulfajnyl-d-C3-al.kyl;
R9 and R10 may be the same or different represents hydrogen, cyano, Ci-C6-alkyl, d-C6- halogenoalkyl, d-C6-alkoxy, d-C6-halogenoalkoxy, d-C6-alkylcarbonyl, d-C6- aikoxycarbony!, d-C6-halogenoa!koxycarbonyl, Ci-C6-alkylaminocarbonyl, d-C6-di- alkylaminocarbonyl, d-d-alkylsulfanyl, C3-C6-carbocycle, CVd-heterocycle; or
R9 and Rl together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members 2
selected from the group consisting of C(=0), C(=S), S(0)m and Si(R )2, may form a five to seven membered ring, which for its part may be substituted by one or more of R' ; n represents 0-1 and m represents 1-2; and provided that the following compounds are excluded from Formula (I),
1) N-(4-(3,5-bis(trifluoromethyI)-lH-pyrazol^^
carbothioamide, 4-methyl-N-phenyl-l,2,3-thiadiazole-5-carbothioamide, N-(3-chloro-4- niethyl.phenyl.)-4-cyclopropyl-l.,2,3-thiadiazole-5-carbothioaniide, 4-cyclopropyl-N-(2,4- dimethoxyphenyl)-l,2,3-thiadiazole-5-carbothioamide, N-(4-(3,5-bis(trifluoromethyl)- l H-pyrazol-l-yl)phenyl)-4-methyl-l,2,3-thiadiazole-5-carbothioamide, N-(4,4- difluorobut-3-en-l-yl)-4-phenyl-l,2,3-thiadiazole-5-carbothioarriide;
2) T= N(R5), N(OR5), N-N(R5)(R6), R1 ^ hydrogen or methyl and Z is not substituted with R8a in Formula (I);
3) T=0, R*= hydrogen, d-Ce-alkyl or cyclopropyl and Z is not substituted with RSa in Formula (I).
4) the Formula A :
Figure imgf000007_0001
Formula A wherein
Rla from d-C6- alkyl halides;
R a, R a and R4a selected from hydrogen, halogens, cyano, Nitro, d-C6-halogenated alky], CrC6-alkoxy, amino sulfonyl halides, d-C6-sulfoxide base, d-d-sulfone, Ci-d-alkyl sulfonamide, phenyl, 1 -5 same or different R"" substituted phenyl containing from 1 -3 same or different and selected from the oxygen atoms, nitrogen or sulfur atoms a 5-or-6- membered heterocyclic ring, 1-4 same or different R"' substituted containing from 1-3 same or different and selected from the oxygen atoms and nitrogen atoms or sulfur atoms of 5-or 6-membered ring, with the proviso that the R a, R3a and R4a there can be only one hydrogen; R3a selected from halogens, nitro, nitrile, Ci-Ce-alkyl, C-. -Ce -aikoxy, d-C6-halogenated alkyl or C]-C6-halogenated alkyl radicals. In one another embodiment, Z of compound of general formula (I) is selected from the group consisting of Ci-Ce-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein one or more carbon atoms may be replaced by heteroaioms selected from N, O, and S or fused and/or nonfused carbocycle or fused and/or nonfused heterocycle, wherein one or more heteroaioms is selected from N, O and S and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)m and Si(R2)2, each of these groups are substituted with R8a and optionally substituted by one or more groups of R .
In one another embodiment, substitution R1 of compound of general formula (I) is selected from halogen, halogenoaJkyl selected from -CHC12, -C(Rb)F2, -CHF2, -C(Rb)2-CF3, -CHF-CF3, -CF2- CF3,-CHF-CF2-CF3, -CH2F, haloalkoxyalkyl selected from -C(Rb)2OCF3, -C(Rb)2OCHF2, - C(Rb)2OCH2F, -Ci-Cg-halogenoalkylsulfanyl-Ci-Ci-aikyl seicted from -C(Rb)2SCF3, - CH(Rb)SCF3, -C(Rb)2SCHF2, -CH(Rb)SCHF2, C C8-halogenoalkylsulfinyl-Cj-C2-alkyl selected from -C(Rb)2SOCF3, -CH(Rb)SOCF3, -C(Rb)2SOC(Rb)F2, -CH(Rb)SOC(Rb)F2, C C6-alkyl- sulfonate-C1-C2-alkyl, C¾ -C6-halogenoalkyl-sulfonate-C ¾ -C2-halogenoalkyl, pentafluoro-λ6- sulfanyl-CrC3-alkyl, C3-C6-cycloalkyl-CrC3-alkyl, C3-C6-cycloalkyl-CrC3-halogenoalkyl, C3- Ce-heterocyclyl-Ci-Ca-alkyl, C3-C6-heterocyclyl-CrC3-halogenoalkyl; optionally each of these groups may be substituted by one or more groups of R ;
wherein Rb represents, hydrogen, halogen, CrCe-alkyl, Ci-Ce-haioalkyl; and other substitutions as defined in one of above embodiment.
In one another embodiment, use of the compounds of formula (I) and agronomically acceptable salts, metallic complexes, structural isomers, stereo-isomers, diastereoisomers, enantiomers, tautomers or N-oxides thereof;
Figure imgf000008_0001
wherin R1 is selected from halogen, halogenoalkyl selected from -CHC12, -C(Rb)F2, -CHF2, - C(Rb)2-CF3, -CHF-CF3, -CF2-CF3,-CHF-CF2-CF3, -CH2F, haloalkoxyalkyl selected from - C(Rb)2OCF3, -C(Rb)2OCHF2, -C(Rb)2OCH2F, -C1-C8-halogenoaIkyIsulfanyI-C1-C2-alkyl seicted from -C(Rb)2SCF3, -CH(Rb)SCF3, -C(Rb)2SCHF2, -CH(Rb)SCHF2, Ci-Cg-halogenoalkylsulfinyl- Ci -Cr aikv i selected from -C(Rb)2SOCF3, -CH(Rb)SOCF3, -C(Rb)2SOC(Rb)F2, - CH(Rb)SOC(Rb)F2, Ci-C6-alkyl-sulfonate-CrC2-alkyl, C}-C6-halogenoalkyl-sulfonate-CrC2- halogenoalkyl, pentafluoro- 6-sulfanyl-C1-C3-alkyl, C3-C6-cycloalkyl-CrC3-alkyL C3-C6- cycloalkyl-Ci-Cirhalogenoalkyl, Ca-Ce-heterocyclyi-Ci-Cs-alkyl, Cs-Ce-heterocyclyi-Ci-Cs- halogenoalkyl; optionally each of these groups may be substituted by one or more groups of R' ; wherein ¾ represents, hydrogen, halogen, CrC6-alkyl, Ci-Ce-haloaikyl; and other substitutions as defined in one of above embodiment,
for controlling of or preventing against phytopathogenic fungi, bacteria and nematodes of agricultural crops and or horticultural crops.
In one another embodiment, substitution T of compound of general formula (I) is S.
In one another embodiment preferred compound of general formula (I) are:
4-(difluoromethyl)-N-(3-(pentafluoro-1.6-sulfaneyl.)phenyl.)-l ,2,3-thiadiazole-5-carboxamide; 4- (difluoromethyl)-N-(3-( entafluoro-16-sulfaneyl^ 4- (difluoromethyl)-N-(4-(pentafl.uoro-16-sulfaneyl)phenyl)-l,2,3-thiadiazole-5-carboxaiTiide; 4- (difluoromethyl)-N-(4-(pentafluoro-16-sulfaneyl)phenyl)- 1 ,2,3-thiadiazole-5-carbothioamide; N- (2-chloro-4-(pentafluoro-16-sulfaneyl)phenyl)-4-(difl.uoromethyl)-l ,2,3-thiadiazole-5- carboxamide; N-(2-chloro-4-(pentafluoro-16-sulfaneyl)phenyl)-4-(difluoromethyl)- 1,2,3- thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-methyl-N-(3-(pentafluoro-16- sulfaneyl)phenyl)-l ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-metliyI-N-(3- (pentafluoro-16-sulfaneyl)phenyl)-l,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N- methyl-N-(4-(pentafluoro-16-sulfaneyl)phenyI)-l,2,3-thiadiazole-5-cai"boxarnide; 4-- (difluoromelhyl)-N-methyl-N-(4-(pentafluoro-16-sulfaneyl)phenyl)-l,2,3-thiadiazole-5- carbothioamide; N-(2-chloro-4-(pentafluoro-16-suIfaneyl)phenyl)-4-(difluoromethyl)-N-methyl- l,2,3-thiadiazole-5-carboxamide; N-(2,6-dichloro-4-(pentafluoro-16-sulfaneyl)phenyl)-4- (difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(2,6-dibromo-4-(pentafluoro-16- sulfaneyl)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxarriide; N-(2-bromo-4- (pentafluoro-16-sulfaneyl)phenyl)-4-(difl.uoromethyl)-l ,2,3-thiadiazole-5-carboxarmde; N-(2- bromo-4-(pentafluoro-16-sulfaneyl)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carbothioamide; 4-(difluoromethyl)-N-(4-(methylthio)-3-(pentafluoro-16-sulfaneyl)phenyl)- l,2,3-thiadiazole-5-carboxamide; 4-(difluorometliyl)-N-(4-(methylthio)-3-(pentafluoro-16- sulfaneyl)phenyl)-l ,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(4-fluoro-3-
(pentafluoiO-16-sulfaneyl)phenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(4- fluoro-3-(pentafluoro-16-sulfaneyl)phen 4-
(difluoroniethyl.)-N-(4-methoxy-3-(pentafluoro-16-sulfaneyl.)phenyl)-l ,2,3-thiadiazole-5- carboxamide; 4-(difluoromethyl)-N-(4-methoxy-3-(pentafluoro-16-sulfaneyl)phenyl)- 1,2,3- thiadiazole-5-carbothioamide; N-(3-(pentafluoro-16-sulfaneyl)phenyl)-4-(trifluoromethyl)- 1,2,3- thiadiazole-5-carboxamide; N-(3-(pentafluoro-16-sulfaneyl)phenyl)-4-(trifluoromethyl)- 1,2,3- thiadiazole-5-carbothioamide; N-(4-(pentafluoro-16-sulfaneyl)phenyl)-4-(trifluoromethyl)- 1,2,3- thiadiaz.ole-5-carboxamide; N-(4-(pentafluoro-16-sulfaneyl)phenyl)-4-((rifluoromethyl)- 1,2,3- thiadiazole-5-carbothioamide; N-(2-chloro-4-(pentafluoro-16-sulfaneyl)phenyl)-4- (trifluoromethyl)- l,2,3-miadiazole-5-carboxamide; N-(2-chloro-4-(pentafluoro-16- sulfaneyl)phenyl)-4-(trifluoroniethyl)-l,2,3-thiadiazole-5-carbothiOarnide; 4-methyl.-N-(3- (pentafluoro-16-sulfaneyl)phenyl)- l,2,3-thiadiazole-5-carboxamide; 4-methyl-N-(3-(pentafluoro- 16-sulfaneyl)phenyl)-l ,2,3-thiadiazole-5-carbothioamide; 4-methyl-N-(4-(pentafluoro-16- sulfaneyl)phenyl)-l ,2,3-thiadiazole-5-carboxamide; N-(2-chloro-4-(pentafluoro-16- sulfaneyl)phenyl)-4-methyl-l,2,3-thiadiazole-5-carboxamide; 4-isopropyl-N-(3-(pentafluoro-16- sulfaneyl)plienyl)-l,2,3-thiadiazole-5-carboxaniide; 4-isopropyl-N-(3-(pentafluoro-!6- siilfaneyl)phenyl)-l,2,3-ihiadiazole-5-carbothioaniide;; 4-isopropyl-N-(4-(pentafluoro-16- sulfaneyl)phenyl)-l ,2,3-thiadiazole-5-carboxamide; 4-isopropyI-N-(4-(pentafluoro-16- sulfaneyl)phenyl)-l,2,3-thiadiazole-5-carbothioamide;; 4-(difluoromethyl)-N-(3- (( fl.uoromethyl)thio)phenyl)-l,2,3-thiadiazole-5-carboxarnide; 4-(difluoromethyl)-N-(3- (( fluoromediyl)thio)phenyl)-l,2,3-thiadiazole-5-carbot ioainide;; 4-(difluoromethyl)-N-(4- ((trifluoromethyl)thio)phenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(4- ((trifluoromethyl)thio)phenyl)- l,2,3-tliiadiazole-5-carbothioamide;; N-(2-chloro-4- ((trifluoromethyl)thio)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxaniide; N-(2-chloro- 4-((trifluoromethyl)thio)phenyl)-4-(difkioromethyl)-l,2,3-thiad N-(4- cMoro-3-((trifluoromethyl)thio)phenyl)-4-(^ N- (2-bromo-5-((trifluoromethyl)mio)phenyl)-4-(dffl^
N-(2-bromo-4-((trifluoromethyl)thio)phenyl)-4-(difluoromet yl)-l,2,3-thiadiazole
carboxamide; 4-(trifluoromethyl)-N-(4-(( fl.uoromethyl)thio)phenyl)-l,2,3-thiadiazole-5- carboxamide; 4-(trifluoromethyl)-N-(4-((trMuoromethyl)thio)phenyl)-l,2,3-thiadiazole-5- carbothioami.de;; 4-(difluoromethyl)-N-(4-((trifluoromethyl)sulfi.nyl.)phenyl.)-l ,2,3-thiadi.azole-5- carboxamide; N-(2-chloro-4-((trifluorometliyl)sulfinyl)phenyl)-4-(difluoromethyl)- 1,2,3- thiadiazole-5-carboxamide; N-(2-bromo-4-((tri.fluoromethyl)sulfinyl)phenyl)-4-(difl.uoromethyl)- l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3-((trifluorometliyl)sulfinyl)phenyl)- l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3-((trifluoromethyl)sulfonyl)phenyl)- 1 ,2,3 -thiadiazole-5-carboxamide; N-(2-bromo-5-((trifluoromethyl)su!fonyl)phenyl)-4- (diiluoromethyl)-l ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3- (methylthio)phenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3- (methylthio)phenyl)- 1 ,2,3-thiadiaz.ole-5-carbothioamide; 4-(difluoromethyl)-N-(4- (methylthio)phenyl)- l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(4- (methylthio)phenyl)-l,2,3-t iadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(2-fluoro-4- (methylthio)phenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2-fluoro-4- (meihylthio)phenyl)-l,2,3-ihiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(2-fluoro-4- (methylthio)phenyl)- 1 ,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(4- (methylsulf onyl)phenyl .)- 1 ,2,3 -thiadiazole-5-carboxamide ; 4-(difluoromethyl) -N-(4-
(methylsulfonyl)phenyl)-l,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(3- (methylsulfinyl)phenyl)- l,2,3-tliiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3- (me(hylsulfonyl)phenyl)-l ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3- (methylsulf onyl)phenyl .)- 1 ,2,3 -thiadiazole-5-carbothioamide; 4-(difluoromethyl) -N-(2-
(trif uoromethoxy)phenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2- (trifl.uoromethoxy)phenyl)-1.,2,3-thiadiazole-5-carbothioamide; N-(4-bromo-2- ( fluoromet oxy)phenyl)-4-(difluoromethyl)-l,2,3-t iadiazole-5-carboxainide; N-(4-bromo-2-
Figure imgf000011_0001
(difluoromethyl)-N-(3-(trifluoromethoxy)phenyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4- (difiuoroniethy])-N-(3^ 4- (difluoromethyl)-N-methyl-N-(3-(trifluorome&^ 4- (difluoromethyl)-N-methyl-N-(3-(trifluorom
N-(2-c oro-5-(trifluoromethoxy)phenyl)-4-(diflu^
N-(2-chloro-5-(trifluoromethoxy)phenyl)-4-(difluoromethyl)-l,2,3-t iadiazole-5- carbothioamide; N-(2,4-dichloro-5-(trifluoromethoxy)phenyl)-4-(difluoromethyl)- 1,2,3- thiadiaz.ole-5-carboxamide; N-(2,4-dichloro-5-(trifluoromethoxy)phenyl)-4-(difluoromethyl)- l,2,3-thiadiazole-5-carbothioamide; N-(2-bromo-5-(trifluoromethoxy)phenyl)-4- (difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(2-bromo-5-(trifluoromethoxy)phenyl)-4- (difluoromethyl)- 1 ,2,3-thiadiazole-5-carbothioamide; N-(2,4-dibromo-5- ( fluoromet oxy)phenyl)-4-(difluoromethyl)-l,2,3-t iadiazole-5-carboxainide; N-(2,4- dibromo-5-(trifluoromethoxy)phenyl)-4-(difluoro 4- (difluorometliyl)-N-(4-( fluoromethoxy)phenyl)-l,2,3-thiadiazole-5-carboxai'nide; 4- (difluoromethyl)-N-(4-(trifluoromethoxy)phenyl)- l ,2,3-thiadiazole-5-carbothioamide; 4- (difluoromethyl)-N-methyl-N-(4-(trifluoromethoxy)phenyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4- (difluoromethyl)-N-methyl-N-(4-(trifluorom
N-(2-c oro-4-(trifluoromethoxy)phenyl)-4-(diflu^
N-(2-chloro-4-(triiluoromethoxy)phenyl)-4-(difluoromethyl)-l,2,3-t iadiazole-5- carbothioamide; N-(2-bronio-4-(trifluoromethoxy)phenyl)-4-(difl.uoromethyl)-l,2,3-thiadiazole- 5-carboxamide; N-(2-bromo-4-((rifluoromethoxy)phenyl)-4-(difluoroniethyl)- 1 ,2,3-thiadiaz.ole- 5-carbothioamide; N-(2-biOmo-4-(trifluoiOmethoxy)phenyl)-4-(difluoromethyl)-N-methyl- 1,2,3- thiadiazole-5-carboxamide; N-(2-bromo-4-(trifluoromethoxy)phenyl)-4-(difluoromethyl)-N- methyl-l,2,3-thiadiazole-5-carbothioamide; N-(3-(difluoromethoxy)phenyl)-4-(difl.uoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(3-(difluoromethoxy)phenyl)-4-(difluoromethyl)- 1 ,2,3- thiadiazole-5-carbothioaniide; N-(3-(difl.uoromethoxy)phenyl)-4-(difluoromethyl)-N-methyl- l,2,3-thiadiazole-5-carboxamide; N-(3-(difluoromethoxy)phenyl)-4-(difluoromethyl)-N-methyl- l,2,3-thiadiazole-5-carbothioamide; N-(2,4-dichloro-5-(difluoromethoxy)phenyl)-4- (difluoromethyl)-l ,2,3-thiadiazole-5-carboxamide; N-(4-(difluoromethoxy)phenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(4-(difluoromethoxy)phenyl)-4- (difluoromethyl)- 1 ,2,3-thiadiazole-5-carbothioamide; N-(4-(difluorometlioxy)phenyl)-4- (difluoromethyl)-N-methyl-l,2,3-thiadia.zole-5-carboxamide; N-(2-chloro-4- (difluoroniethoxy)phenyl)-4-(difluoromethyl)-l,2,3-thi diazole-5-carboxarnide; 4- (difluoromethyl)-N-(2-((rifluoromethyl)phenyl)-l,2,3-thiadiazole-5-carboxaini 4- (difluoromethyl)-N-(2-( fl.uoromethyl)phenyl)-l ,2,3-thiadiazole-5-carbothioaniide N-(4- chloro-2-(trifluoromethyl)phenyl)-4-(difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(4- chloro-2-(trifiuoroniethyl)ph^ N- (2,4-dichloro-6-(trifliioromediyi)ph^
N-(4-bromo-2-(trifluorome(hyl)phenyl)-4-(difluorome(hyl)-l,2,3-thiadia^ N- (4-bromo-2-(trifluoromeihyl)phenyl)-4-(difluoromeihyl)-L2,3-thiad N- (4-bromo-2-(trifluoromethyl)phenyl)-4-(difluoromethyl)-N-methyl-l,2,3-thiadiazole-5- carboxamide; 4-(difluoromediyl)-N-(4-fluoro-2-(trifluoromethyl)phenyl)-l,2,3-thiadiazole-5- carboxamide; 4-(difluoromethyl)-N-(4-fluoro-2-(trifluoromethyl)phenyl)-l,2,3-thiadiazole-5- cai'bothioamide; 4-(difluoromethyl)-N-(3-(trifluoromethyl)phenyl)-l,2,3-thiadiazole-5- carboxamide; 4-(difluoromethyl)-N-(3-(trifluoromethyl)phenyl)-l,2,3-thiadiazole-5- carbothioamide; 4-(difluoromethyl)-N-methyl-N-(3-(trifluoromethyl)phenyl)-l,2,3-thiadiazole- 5-carboxamide; N-(2-chloro-3-(trifluoromethyl)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carboxamide; N-(2-chloro-3-( fluoroniethyl)phenyl)-4-(difluoroniethyl)-l ,2,3-thiadiazole-5- carbothioamide; N-(4-chloro-3-(ti"ifluoromethyl)phenyl)-4-(difluoromethyl)-l,2,3-tliiadiazole-5- carboxamide; N-(4-chloro-3-(trifluoromethyl)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carbothioamide; 4-(difluoiOmethyl)-N-(4-(trifluoromethyl)phenyl)- 1 ,2,3-thiadiazole-5- carboxamide; 4-(difluoromethyl)-N-(4-(trifluoromethyl)phenyl)-l,2,3-thiadiazole-5- carbothioamide; 4-(difluoromethyl)-N-methyl-N-(4-(trifluoiOmethyl)phenyl)- l,2,3-thiadiazole- 5-carboxamide; N-(2-chloro-4-(triiluorome(hyl)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carboxamide; N-(2-chloro-4-(trifluoromethyl)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carbothioamide; N-(2,6-dichloro-4-((rifluoromethyl)phenyl)-4-(difluoromethyl)- 1 ,2,3- thiadiazole-5-carboxamide; N-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(difluoromethyl)- l,2,3-thiadiazole-5-carbothioamide; N-(2-bromo-4-(trifluoromethyl)phenyl)-4-(difluoromethyl)- l,2,3-ihiadiazole-5-carboxamide; N-(2-bromo-4-(trifluoromethyl)phenyl)-4-(difluoromethyl)- l,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(2-fluoro-4-(trifluoromethyl)phenyl)- l ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2-fluoro-4-(trifluoromethyl)phenyl)- 1 ,2,3 -thiadiazole-5-carbothioamide; N-(3 ,5-bis(trifluoromethyl)phenyl) -4-(difluoromethyl)- l,2,3-thiadiazole-5-carboxamide; N-(3,5-bis(trifluoromethyl)phenyl)-4-(difluoromethyl)- 1,2,3- t adiazole-5-carbodiioamide; 4-(difluoromethyl)-N-(2-metiiyl-4-(perfluoropropan-2-yl)phenyl)- l,2,3-thiadiazole-5-carboxamide; N-(2-chlorophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carboxamide; N-(2-chlorophenyl)-4-(difluoromethyl) - 1 ,2,3-thiadiazole-5-carbothioamide; N- (2,4-dichlorophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(2,4- dichlorophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N- (2,4,6-trichlorophenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2,4,6- trichlorophenyl)-l,2,3-thiadiazole-5-carbothioamide; N-(2,3-dichlorophenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(2,3-dichlorophenyl)-4-(difluoromethyl)- 1 ,2,3-thiadiazole-5-carbothioamide; N-(2,5-dichlorophenyl)-4-(difluoromethyl)- 1 ,2,3- thiadiaz.ole-5-carboxamide; N-(2-chloro-4-methylphenyl)-4-(difluoromethyl)-l,2,3-thiadiaz.ole- 5-carboxamide; N-(3-chlorophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(3- chlorophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carbothioai'nide; N-(3,4-dichlorophenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(3,4-dichlorophenyl)-4-(difluoromethyl)- l,2,3-thiadiazole-5-carbothioamide; N-(3,5-dichlorophenyl)-4-(difluoromethyl)- 1,2,3- thiadiaz.ole-5-carboxamide; N-(3-chloro-4-methylphenyl)-4-(difluoromethyl)-l,2,3-thiadiaz.ole- 5-carboxamide; N-(3-chloro-4-methylphenyl)-4-(difluoiOmethyl)-l,2,3-thiadiazole-5- carbothioamide; N-(4-chlorophenyl)-4-(difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(4- chlorophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; N-(2-bromophenyl)-4- (difluoromethyl)- 1 ,2,3 -thiadiazole-5 -carboxamide; N-(2-bromophenyl)-4-(difluoromethyl)- 1 ,2,3- thiadiazole-5-carbothioaniide; N-(2-bromo-5-chlorophenyl)-4-(difl.uoromethyl)- 1,2,3- thiadiazole-5-carboxamide; N-(2-biOmo-5-chlorophenyl)-4-(difluoromethyl)-l,2,3-tliiadiazole-5- carbothioamide; N-(2,4-dibromophenyl)-4-(difluoromethyl)-l.,2,3-thiadiazole-5-carboxamide; N- (2,4-dibromophenyl)-4-(dif luorometliyl)- 1 ,2,3-ihiadiazole-5-carbothioamide; 4- (difluoromethyl)-N-(2,4,6-tribromophenyl)-l,2,3-thiadiazole-5-carboxarnide; N-(2-bromo-4- fluorophenyl)-4-(difluoromethyl)-l,2,3-tiiiadiazole-5-carboxamide; N-(2-bromo-4- fluorophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; N-(2-bromo-3- methylphenyl)-4-(difl.uoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(3-bromophenyl)-4- (difluoromethyl)- 1 ,2,3 -thiadiazole-5 -carboxamide; N-(3-bromophenyl)-4-(difluoromethyl)- 1 ,2,3- thiadiazole-5-carbothioamide; N-(4-bromophenyl)-4-(difluoromethyl)-l,2,3-tliiadiazole-5- carboxamide; 4-(difluoromethyl)-N-(2-fluorophenyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4- (difluoroniethyl)-N-(2-fluorophenyl)-1.,2,3-thiadiazole-5-carbothioamide; N-(4-chloro-2- fluorophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(4-chloro-2- fluorophenyl)-4-(difluoromethyl)-l ,2,3-thiadiazole-5-carbothioamide; N-(3-chloro-2- fluorophenyl)-4-(difluoromethyl)-l,2,3-tliiadiazole-5-carboxamide; N-(3-chloro-2- fluorophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; N-(4-bromo-2- fluoiOphenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-cai"boxaniide; N-(4-bromo-2- fluorophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carbothioaniide; N-(3-bromo-2- fluorophenyl)-4-(difluoromethyl)-l,2,3-tliiadiazole-5-carboxamide; N-(3-bromo-2- fluorophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N- (2,6-difluorophenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2,6- difluorophenyl)-l,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(2-fluoro-4- methylphenyl)-1.,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3-fluorophenyl)- 1 ,2,3- thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3-fluorophenyl)- 1 ,2,3-thiadiazole-5- carbothioamide; 4-(difluoromethyl)-N-(3,4-difluorophenyl)-l,2,3-thi diazole-5-carboxarnide; 4- (difluoromethyl)-N-(3,4-difluorophenyl)-l,2,3-thiadiazole-5-carbothioaniide; 4- (difluoromethyl)-N-(4-fluorophenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(4- fluorophenyl)- l,2,3-thiadiazole-5-carbothioamide; N-(4-bromo-2-methylphenyl)-4- (difluoromethyl)-l ,2,3-thiadiazole-5-carboxamide; N-(4-bromo-2-methylphenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(4-fluoro-2- methylphenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(4-fluoro-2- methylphenyl) - 1 ,2,3-thiadiazole-5-carbothioarnide; 4-(difluoromethyl)-N-(p-tolyl)- 1 ,2,3 - thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-^-tolyl)-l,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(perfluorophenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N- (perfluorophenyl)- 1 ,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(2,3,5,6- tetrafluorophenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2,3,5,6- tetrafluorophenyl)-l,2,3-thiadiazole-5-carbothioarnide; N-(2-cyanophenyl)-4-(difluoromethyl)- l,2,3-thiadiazole-5-carboxamide; N-(4-chloro-2-methoxyphenyl)-4-(difluoromethyl)- 1,2,3- thiadiazole-5-carboxamide; N-(4-chloro-2-methoxyphenyl)-4-(difluoromethyl)- 1 ,2,3 -thiadiazole- 5-carbot ioamide; 4-(difluoromethyl)-N-(3-methoxyphenyl)-l,2,3-thiadiazole-5-carboxamide; 4- (difluoromethyl)-N-(3 -methoxyphenyl)- 1 ,2,3-thiadiazole-5-carbothioamide; N-(2-chloro-3- met oxyphenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(4- methoxyphenyl)-l,2,3-thiadiazole-5-carboxaiTiide; 4-(difluoromethyl)-N-(4-methoxyphenyl)- 1 ,2,3-thiadiazole-5-carbothioamide; N-(2-chloro-4-methoxyphenyl)-4-(difluoromethyl)- 1 ,2,3- thiadiazole-5-carboxamide; N-(2-chloro-4-methoxyphenyl)-4-(difluoromethyl)- l,2,3-thiadiazole- 5-carbothioamide; N-(2-chloro-4-^entafluoro-16-sulfaneyl)phenyl)-4-methyl-l,2,3-t]iiadiazole- 5-carbothioamide; 4-methyl-N-(3-((trifluoromethyl)thio)phenyl)-l,2,3-thiadiazole-5- carbothioamide; 4-methyl-N-(4-((trifluoroniethyl)thio)phenyl)-l,2,3-thiadiazole-5- carbothioami.de; 4-methyl-N-(3-(trifluoromethoxy)phenyl)-l,2,3-thiadiazole-5-carbothioamide;
4- memyl-N-(4-( fluoromemoxy)phenyl)- l,2,3-thiadiazole-5-carbothioamide; N-(2-chloro-4- ( fl.uoromemoxy)phenyl)-4-methyl.-l ,2,3-thiadiazole-5-carbothioaniide; N-(3- (difluoromethoxy)phenyl)-4-methyl- l,2,3-thiadiazole-5-carbothioamide; N-(4- (difluoromethoxy)phenyl)-4-methyl-l,2,3-thiadiazole-5-carbothioamide; N-(3-fluorophenyl)-4- methyl- l,2,3-thiadiazole-5-carbothioamide; 4-methyl-N-(4-(methyltliio)phenyl)- 1,2,3- thiadiazole-5-carbothioamide; 4-isopropyl-N-(3-((trifluoromethyl)thio)phenyl)-l,2,3-thiadiazole-
5- carbothioamide; 4-(difluoromethyl)-N-phenyl- 1 ,2,3-thiadi.azole-5-carboxamide; 4- (difluoromethyl)-N-phenyl-l,2,3-thiadiaz.ole-5-carboxamide; 4-(difluoromethyl)-N-(2- nitrophenyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3-nitrophenyl)- 1 ,2,3- thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(4-nitrophenyl)-l,2,3-thiadiazole-5- carboxamide; 4-(difluorom.ethyl)-N-(4-nitrophenyl.)-l ,2,3-thiadiazole-5-carbothi.oamide; N-(5- bromopyridin-2-yl)-4-(dMuoromemyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N- (pyridin-3-yl)-l,2,3-thiadiazole-5-carbothioamide; N-(6-chloropyridin-3-yl)-4-(difluoromethyl)- 1 ,2,3 -thiadiazole-5-carbothioamide; N-(5,6-dichloropyridin-3-yl)-4-(difluoromethyl)- 1 ,2,3- thiadiazole-5-carbothioamide; N-(5-bromo-2-chloropyridin-3-yl)-4-(difluoromethyl)- 1,2,3- thiadiazole-5-carbothioamide; N-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-4-(difluoromethyl)- 1 ,2,3-thiadiazole-5-carbothioamide; 4-methyl-N-(3'-(pentafluoro-16-sulfaneyl)-[ 1 , Γ-biphenyl] -2- yl)- 1 ,2,3 -thiadiazole-5-carbothioamide; 4-isopropyl-N-(3'-(pentafluoro-16-sulfaneyl)-[l,r- biphenyl]-2-yl)-l,2,3-thiadiazole-5-carbothioamide; 4-isopropyl-N-methyl-N-(3'-(pentafluoro-16- sulfaneyl)-[l,l.'-biphenyl]-2-yl)-l,2,3-thiadiaz.ole-5-carbothioamide; 4-(difluoromethyl)-N-(3'- (pentafluoro-16-sulfaneyl)-[l,l'-biphenyl]-2-yl)-l,2,3-thiadiazole-5-carbomioamide; 4- (difluoromemyl)-N-(3'-(pentafluoro-16-sulfaneyl)-[ l,r-biphenyl]-2-yl)-l ,2,3-thiadiazole-5- cai'bothioamide; (E)-N-(2-(N-cyano-S-isopropylsulfinimidoyl)phenyl)-4-methyl- 1,2,3- thiadiazole-5-carboxamide; N-(4'-(N-ethyl-S-methylsulfonimidoyl)- [1,1 -biphenyl] -2-yl)-4- methyl- l,2,3-thiadiazole-5-carboxamide; N-(4'-(N-(cyclopropylmetliyl)-S-methylsulfonimidoyl)- [1 , r-biphenyl]-2-yl)-4-methyl- 1 ,2,3-thiadiazole-5-carboxamide; (E)-N-(3-(N-cyano-S- isopropylsulfinirmdoyl)phenyl)-4-(difluoromethyl)- l,2,3-miadiazole-5-carboxamide; N-(4-(N- cyanopropan-2-ylsulfonimidoyl)phenyl)-4-(diiluoromethyl)-l ,2,3-thiadiazole-5-carboxamide; N- cyclohexyl-4-(difluoromethyl)-l,2,3-thi.adiazole-5-carboxamide; N-cyclohexyl-4- (difluoromethyl)- 1 ,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-isopropyl- 1 ,2,3- thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-isopropyl- 1 ,2,3-thiadiazole-5-carbothioamide; (4-(difluoromethyl)- 1 ,2,3-thiadiazol-5-yl)(morpholino)methanone; (4-(difluoromethyl)- 1 ,2,3- thiadiazol-5-yl)(morpholino)methanethione; (4-(difluoromethyl)-1.,2,3-thiadiazol-5- yl)(thiomorpholino)methanone; (4-(difluoromethyl)- 1 ,2,3-thiadiazol-5- yl)(thiomorpholino)methanethione; (4-(difluoromethyI)-l,2,3-thiadiazol-5-yl)(4- methylpiperazin- 1 -yl)methanone; 4-(chloromethyl) -N-(4- (pentafluoro-16- sulf aneyl)phenyl) - l,2,3-thiadiazole-5-carboxamide; 4-(chloromethyl)-N-(3-(pentafluoro-16-sulfaneyl)phenyl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(3',4'-dichloiO-5-fluoro- [ 1 , Γ-biphenyl] -2-yl)-4-
(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(3',4'-dichloro-5-fluoro-[l,r-biphenyl]-2- yl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(3',4',5'- trifluoro-[ 1 , l'-biphenyl]-2-yl)- 1 ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3',4',5'- trifluoro-[1., -biphenyl]-2-yl)-l,2,3-thiadiazole-5-carbothioamide; 4-(diiiuofoniethyl)-N- methoxy-N-(l-(2,4,6-tricWorophenyl)propan-2-yl)-l,2,3-lMadiazole-5-carboxamide; N-(3',4'- dichloro-5-fluoro-[l, -biphenyl]-2-yl)-4-isopropyl-l,2,3-thiadiazole-5-carboxaniide; 4- isopropyl-N-(3',4',5'-trifluoro-[ 1 , 1 -biphenyl] -2-yl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(2-(3- chloro-5-(trifluoromethyl)pyridm^ N- (4'-chloro-[l, -biphenyl]-2-yl)-4-methyl-l,2,3-thiadiazOle-5-carboxamide; N-(3',4'-dichloro-5- fluoro-[l, -biphenyl]-2-yl)-4-methyl-l,2,3-thiadiazole-5-carboxamide; 4-met yl-N-(3',4',5'- trifluoro-[ 1 , 1 '-biphenyl] -2-yl)- 1 ,2,3-thiadiazole-5 -carboxamide; N-(4'-chloro-[ 1 , 1 -biphenyl]-2- yl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; 4-(dif uoromethyl)-N-(2-(4- methylpentan-2-yl)phenyl)-l,2,3-thiadiazole-5-cai"boxamide; 4-(difluoromethyl)-N-(3- (isopropylthio)phenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3- (isopropylsulfinyl)phenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3- (isopropylsulfonyl)phenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2-(l- (isopropylthio)ethyl)phenyl)-l,2,3-thiadiazole-5-carboxajmide; 4-(difluoromethyl)-N-(2-(l- (isopropylthio)ethyl)phenyl)- 1 ,2,3 -thiadiazole-5-carbothioamide; 4-methyl-N-(4-(pentafluoro-16- sulfaneyl)phenyl)-l ,2,3-thiadiazole-5-carbothioamide; N-(3-chloro-4-methylphenyl)-4-methyl- 1 ,2,3 -ttaadiazole-5-carbothioamide; 4-methyl-N-(m-tolyl)-l,2,3-thiadiazole-5-carbothioamide; N-(3-isopropoxyphenyl)-4-methyl-l ,2,3-thiadiazole-5-carbothioamide; 4-methyl-N-phenyl- l,2,3-thiadiazole-5-carbothioamide; N-(2-chloro-4-(methylsulfonyl)phenyl)-4-(difluoromethyl)- l,2,3-thiadiazole-5-carboxamide; N-(2,6-dichlorophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole- 5-carboxamide; N-(4'-chloro-[l,r-biphenyl]-3-yl)-4-(difluoiOmethyl)- l,2,3-tliiadiazole-5- carboxamide; N-([l,r-biphenyl]-3-yl)-4-(dMuorome(hyl)-l,2,3-thiadiazole-5-carboxamide; N- (3',4'-difluoro-[ l, -biphenyl]-3-yl)-4-(difluoromethyl)-l ,2,3-thiadiazole-5-carboxamide; 4- (difluoromethyl)-N-(3',4',5'-trifluoro-[l, -biphenyl]-3-yl)-l,2,3-thiadiazole-5-ca^^ 4- (difluoromethyl)-N-(3\4'-dimethyl-[ l,^^ N-(4- (difluoromethoxy)phenyl)-4-(difluoromethyl)-N-methyl-l,2,3-thiadiazole-5-carbotM 4- (difluoroniethy])-N-(2-((trifluoromeihyl)thio)phenyl) 4- (difluoromethyl)-N-(2-((trifluoromefo^ N-(4- bromo-2-((trifluoromethyl)thio)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5 N- (2,4--dibromo--6-((trifhioro
carboxamide; N-(4-chloro-2-((trifm^
5-carboxamide; N-(2,4-dichloro-6-((trifluoromethyl)thio)phenyl)-4-(difluoromethyl)- 1,2,3- thiadiazole-5-carboxamide; N-(2-chloro-4-((trifluoromethyl)sulfonyl)phenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(4- ((trifluoromet yl)sulfonyl)phenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3- ((trifl.uoromethyl)sulfinyl)phenyl)-l ,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(3- nitrophenyl)- 1 ,2,3-t iadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(2-nitrophenyl)- 1 ,2,3- thiadiazole-5-carbothioaniide; N-(2-bromo-5-((trifluoromethyl)thio)phenyl)-4-(difluorornethyl)- l,2,3-thiadiazole-5-carbothioamide; N-(2-bromo-4-((trifluoromethyl)thio)phenyl)-4- (difluoroniethy])-l ,2,3-ihiadiazo}e-5-carbothioaniide; 4-(difluoromethyl)-N-(4- (( fluoromediyl)sulfinyl)phenyl)-l,2,3-thiadiazole-5-carbothioaniide; 4-(difluoromethyl)-N-(3- ((trifluoromethyl)sulfonyl)phenyl)-l ,2,3-(hiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(4- ((trifluoromethyl)sulfonyl)phenyl)-l ,2,3-thiadiazole-5-carbothioamide; N-(2,6-dibromo-4- ((trifluoromethyl)thio)phenyl)-4-(diflu^ N-(3- (pentafluoro 6-sulfaneyi)ph^
carboxamide; N-(4-(pentafluoro-16-sulfaneyl)phenyl)-4-(((trifluoromethyl)diio)methyl)- 1,2,3- thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(4-(dimethylamino)phenyl)- 1 ,2,3-thiadiazole- 5-carboxamide; 4-(difluoromelhyl)-N-(4-(dimethylar]iino)phenyl)-l,2,3-thiadiazole-5- carbothioamide; N-(4-(tert-butyl)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxarnide; N-(4-(tert-butyl)phenyl)-4-(dMuoromet yl)-l,2,3-t adiazole-5-carbothioarnide; N-(2~bromo-4- ((trifluoromethyl)sulfinyl)phenyl)-4-(dffl N-(4- chloro-2-((trifluoromethyl)thio)phenyl)-4-(difluoromethyl)- l,2,3-thiadi
4-(difluoromethyl)-N-(2-((trifl^ 4- (difluoromethyl)-N-(4-((difluoromemyl)th^ N-(4- bromo-2-((trifluorom
4-(difluoromemyl)-N-(4-((difluoromethyl)t N- (4-bromo-2-((trifluoromethyl)mio)pheny
carbothioamide; N-(2-chloro-4-(pentafl.uoro-16-sulfaneyl)phenyl)-4-(chloromethyl)- 1,2,3- thiadiaz.ole-5-carboxamide; N-(4-bromophenyl)-4-(difluoromethyl)- 1 ,2,3-thiadiazole-5- carbotiiioamide; 4-(difluoromethyl)-N-(2,4,6-tribromophenyl)-l,2,3-tliiadiazole-5- carbothioamide; N-(3,5-dic orophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; N-(2-cyanophenyl)-4-(difluoromethyl)-l.,2,3-thiadiazole-5-carbothioamide; N-(2,5- dichlorophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; N-(2,6-dichlorophenyl)- 4-(difl.uoromethyl)-l,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(perbromophenyl)- 1 ,2,3 -thiadiazole-5-carboxamide; N-(2,6-dibromo-4-nitiOphenyl)-4-(difluoromethyl)- 1 ,2,3- thiadiazole-5-carboxaniide; N-(3,5-dibromop enyl)-4-(difluorometiiyl)-l,2,3-t adiazole-5- carboxamide; 4-(diiluorometiiyl)-N-(2,3,4-tribi mophenyl)-l,2,3-t adiazole-5-carboxamide; N- (3,4-dibromophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(2,5- dibromophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(3,4-dibromophenyl)-4- (difluoromethyl)-l,2,3-(hiadiazole-5-carbothioaniide; N-(3,5-dibromophenyl)-4- (difluoromethyl)-l ,2,3-thiadiazole-5-carbothioamide; N-(2,5-dibromophenyl)-4- (difluoromethyl)- 1 ,2,3-thiadiazole-5-carbothioamide; N-(2,6-dibromo-4- (trifluoromethyl)phenyl)-4-(difluoromethyl)-l.,2,3-thiadiazole-5-carboxamide; N-(2-bromo-6- chloro-4-(trifluoromethyl)phenyl)-4-(difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(2- bromo-6-fluoro-4-(trifluoromethyl)phenyl)-4-(dffl^
N-(3-chloro-5-((trifluoromethyl)thio)pyri^
carboxamide; N-(4-chloro-2-(trifluoromethoxy)phenyl)-4-(difl^
carboxamide; N-(4-chloro-2-(trifluorometlioxy)phenyl)-4-(difluoiOmetliyl)-l,2,3-tliiadiazole-5- carbothioamide; 4-(difluoromethyl)-N-(2-methyl-4-(perlluoropropan-2-yl)phenyl)- 1,2,3- t adiazole-5-carbothioamide; (4-(difluoromethyl)-l,2,3-thiadiazol-5-yl)(4-phenyl-3,6- dihydropyridin-l(2H)-yl)methanone; N-(2,6-dibromo-4-(trifluoromethoxy)phenyl)-4- (difluorometliyl)-l,2,3-thiadiazole-5-carboxamide; N-(2,4-dibromo-6- ((rifluoromethoxy)phenyl)-4-(difluoromet yl)-l,2,3-thiadiazOle-5-carboxamide; N-(2,4- dibronio-6-(trifluoromethoxy)phenyl)-4-(difi^ N- allyl-4-(difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(prop-2-yn- 1 - yl)-l ,2,3-thiadiazole-5-carboxamide; N-(2-bromo-6-niethyl-4-(perfluoropropan-2-yl)phenyl)-4- (difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(2-chloro-4- ((trifluoromeihyl)sulfm^ N-(2- biOmo-4-((trifluoromethyl)sulfonyl)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carbothioamide; N-(2,6-dibromo-4-((trifluoromethyl)thio)phenyl)-4-(difluoromethyl)- 1,2,3- thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(4-((difluoromethyl)sulfonyl)phenyl)- 1,2,3 - thiadiazole-5-carboxamide; 4-(difluoromet yl)-N-(4-((difluoromethyl)sulfonyl)phenyl)- 1,2,3- thiadiazole-5-carbothioamide; 4-(chloromethyl)-N-(3-(tri.fluoromethoxy)phenyl)- 1,2,3- thiadiaz.ole-5-carboxamide; N-(2-chloro-4-((difluoromethyl)thio)phenyl)-4-(difluoromethyl)- l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(4-((difluoiOmetliyl)sulfinyl)phenyl)- l,2,3-thiadiazole-5-carboxamide; N-(2,6-dichloro-4-(trifluoromethoxy)phenyl)-4- (difluoromethyl)-l ,2,3-thiadiazole-5-carboxamide; N-(2,4-dichloro-6-(trifluoromethoxy)phenyl)- 4-(difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(4- ((difluoromethyl)sul inyl)phenyl)- 1 ,2,3-thiadiazole-5-carbomioamide; N-(2-chloro-4- (trifluoromethyl)phenyl)-4-(chloromethyl)-l ,2,3-thiadiazole-5-carboxamide; N-(2-chloro-4- (difluoroniethoxy)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; N-(2,6- dibromo-4-(trifluoromethyl)phenyl)-4-(difluoromem^ N- (2-bromo-6-chloro-4-(trifluorome(hyl)phenyl)-4-(difluorome(hyl)-l,2,3-thiadiaz^
carbothioamide; N-(2-bromo-6-f luoro-4- -(trifluoromethyl)phenyl)-4-(difluoromethyl)- 1 ,2,3 - thiadiazole-5-carbothioamide; N-(3,5-dibromopyridin-2-yl)-4-(difluoromethyl)- 1,2,3- thiadiazole-5-carboxaniide; 4-(difl.uoromethyl)-N-(4-nitro-3-(trifluoromethyl)phenyl)- 1,2,3- thiadiaz.ole-5-carboxamide; N-(2-cyclopropyl-4-(trifluoromethyl)phenyl)-4-(difluoromethyl)- l ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2-fluoro-5-(trifluoromethyl)phenyl)- l,2,3-thiadiaz.ole-5-carboxamide; N-(5-chloro-6-(methylthio)pyridin-3-yl)-4-(difluoromethyl)- l,2,3-thiadiazole-5-carboxamide; N-(2-bromo-4-(difluoromethoxy)phenyl)-4-(difl.uoromethyl)- l,2,3-thiadiazole-5-carboxamide; N-(2-bromo-4-(difluoromethoxy)phenyl)-4-(difluoromethyl)- l,2,3-thiadiazole-5-carbothioamide; N-(2,4-dichloro-5-(difluoromethoxy)phenyl)-4- (difluoromethyl)- 1 ,2,3-thiadiazole-5-carbotliioamide; N-(2,6-dibromo-4- ((trifluoromethyl)sulfinyl)phenyl)-4-(difl^ N-(2,6- dibromo-4-((trifluoromethyl)sulfonyl)phenyl)-4-(difluoromethyl)- 1,2,3 -thiadiazole-5- carboxamide; N-(2-bromo-6-chloro-4-((trifluoromethyl)thio)phenyl)-4-(difluoromethyl)- 1,2,3- thiadiazole-5-carboxamide; N-(2,6-dic oiO-4-((trifluoromethyl)thio)phenyl)-4-(difluoromethyl)- l,2,3-thiadiazole-5-carboxamide; N-(2-bromo-6-chloro-4-(((rifluoromethyl)thio)phenyl)-4- (difluoromethyl)- 1 ,2,3-thiadiazole-5-carbothioamide; N-(2,6-dichloro-4- ((trifliioromediyl)thio)phenyl)-4-(difluoromethyl)-l,2,3-ihiadi N- ^enzo[d]isothiazol-5-yl)-4-(dif!uorometiiyl)-l,2,3-thiadiazole-5-carboxajmide; N-(5-chloro-6- (methylsulfonyl)pyridin-3-yl)-4-(difluoromethyl)-l,2,3-tliiadiazole-5-carboxamide; (4- (difluoromethyl)- 1 ,2,3-thiadiazol-5-yl)(2,2,4-trimethylquinolin- 1 (2H)-yl)methanone; N-(3- chlorophenyl)-4-(fluorometliyl)-N-metliyl- 1 ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)- N-(2-fluoro-3-(trifluoromethyl)phenyl)-l,2,3-thiadiazole-5-carboxamide; (4-(difluoromethyl)- l,2,3-thiadiazol-5-yl)(3,4-dihydiOquinolin-l(2H)-yl)methanone; N-(2,4-dichlorophenyl)-4- (difluoromethyl)-N-methyl-l,2,3-thiadiazole-5-carboxamide; N-(4-chloro-3-fluorophenyl)-4- (difluoroniethyl)-l ,2,3-thiadiazole-5-carboxamide; N-(3-chloro-4-fluorophenyl)-4- (difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(2,4-dibromophenyl)-4-(difluoromethyl)- N-methyl- 1 ,2,3 -thiadiazole-5-carboxamide; 5-(3-((difluoromethyl)thio)phenyl)-4,5-dihydro-6H- pyrrolo[3,4-d][l,2,3]thiadiazol-6-one; 4-(difluoromethyl)-N-methyl-N-(2,4,6-trichlorophenyl)- l,2,3-ihiadiazole-5-carboxamide; N-(4-chloro-3-fluorophenyl)-4-(difluoromethyl)- 1,2,3- thiadiaz.ole-5-carbothioamide; N-(3-chloro-4-fluorophenyl)-4-(difluoromethyl)-l,2,3-thiadiaz.ole- 5-carbothioamide; N-(4-chloro-2-cyclopropylphenyl)-4-(difluoromethyl)-l ,2,3-thiadiazole-5- carboxamide; N-(2-bromo-4-((trifluorometliyl)sulfinyl)phenyl)-4-(difluoromethyl)- 1,2,3- thiadiazole-5-carbothioamide; N-(2,6-dichloro-4-(pentafluoro-16-sulfaneyl)phenyl)-4- (difluoromethyl)-l ,2,3-thiadiazole-5-carbothioamide; N-(2-bromo-6-chloro-4-(pentafluoro-16- sulfaneyl)phenyl)-4-(difluoromethyl)-l ,2,3-thiadiazole-5-carboxamide; N-(2,6-dichloro-4- (pentafluoiO-16-sulfaneyl)phenyl)-4-(difluoromethyl)-N-methyl-l,2,3-thiadiazole-5- carboxamide; N-(2-cyclopropyl-4-(pentafluoro-16-sulfaneyl)phenyl)-4-(difluoromethyl)- 1,2,3- thiadiazole-5-carboxaniide; N-(2-bromo-6-chloro-4-((trifluoromethyl)sulfinyl)phenyl)-4- (difluoromethyl)- 1 ,2,3 -thiadiazole-5 -carboxamide; N-(2,6-dichloro-4- ((iriiluofomeihyi)sulilny N-(2,6- dibromo-4-(( fluoromethyl)sulfinyl)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole
carbothioamide; N-(2-bromo-6-chloro-4-((trifluoromethyl)sulfinyl)phenyl)-4-(difl.uoromethyl)- l,2,3-thiadiazole-5-carbothioamide; N-(2,6-dichloro-4-((trifluoromethyl)sulfinyl)phenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; N-cyclopropyl-N-(3,5-dichlorophenyl)-4- (difluorometliyl)-l,2,3-thiadiazole-5-carboxamide; N-(2-bromo-4-((difluoromethyl)thio)phenyl)- 4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2- ((difluoiOmethyl)thio)phenyl)-l ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2- ((difluoromethyl)thio)phenyl)-l,2,3-thiadiazole-5-carbothioamide; N-(2-chloro-4- ((difluoromediyl)thio)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carbothioamid^ N-(4- cMoro-2-((dffluoromethyl)thio)phenyl)-4-(diflu^ N- (4-bromo-2-((difluoromethyl)thio)^^
N-(2-chloro-4-((difluoromethyl)sulfinyl)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carboxamide; N-(4-chloro-2-((difluoromethyl)thio)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole- 5-carbothioamide; N-(2-chloro-4-((difluoromethyl)sulfonyl)phenyl)-4-(difluoromethyl)- 1,2,3- thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2-((difluoromethyl)sulfinyl)phenyl)- 1,2,3- thiadiazole-5-carboxamide; (4-(difluoromethyl)- 1 ,2,3 -thiadiazol-5-yl)(2,2,4-trimethyl-3,4- dihydroquinolin-l(2H)-yl)methanone; 4-(fluoromethyl)-N-(3-(trifluoromethyl)phenyl)- 1,2,3- thiadiazole-5-carboxamide; N-cyclopropyl-4-(difluoromethyl)-N-(3-(trifluoromethoxy)phenyl)- l,2,3-thiadiazole-5-carboxamide; N-cyclopropyl-4-(difluoromethyl)-N-(4- (tri†1uorometlioxy)phenyl)-l,2,3-tliiadiazole-5-carboxamide; N-cyclopropyl-4-(difluoromethyl)- N-(3-(trifluoromethoxy)phenyl)- 1 ,2,3-thiadiazole-5-carbothioamide; N-cyclopropyl-4- (difluorometiiyl)-N-(4-(trifluoromeAoxy)pheny N- cyclopropyl-4-(difluoromet yl)-N-(3-( entafluoro-16-sulfai eyl)phenyl)- l,2,3-thiadiazole-5- carboxamide; 4-(fluoromethyl)-N-(4-(trifluoromethyl)phenyl)-l,2,3-thiadiazole-5-carboxaniide; (4-(dffluorome l)-l,2,3-tMadiazol-5-yl)(^
yl)methanone; N-(4'-chloro-[l ,Γ-biphenyl ]-4-yl)-4-(difluoromethyl)-l ,2,3-thiadiazole-5- carboxamide; N-(2,6-dichloro-4-((trifluoromethyl)sulfonyl)phenyl)-4-(difluoromethyl)- 1,2,3 - thiadiazole-5-carboxamide; N-(2-brorao-6-c oro-4-((trifluoromethyl)sulfonyl)phenyl)-4- (difluoromethyl)- l,2,3-thiadiazole-5-carboxamide; N-(2-cyclopropyl-4- ((trifluoromethyl)thio)phenyl)-4-(difluoro 4- (chloromethyl)-N-(4-((trifluoromethyl)t 4- (chloromethyl)-N-(4-fluoro-3-(trifluoro 4- (chloromethyl)-N-(4-(trlfluoromethoxy)phenyl)- l ,2,3-thiadiazOle-5-carboxanii 4- (difiuorc«iiemyl)-N-(2-((difliioro N- (2-chlOro-4-((difluoromethyl)sulfonyl)phenyl)-4-(difl.uoromethyl)-l,2,3-thiadiazole-5- carbothioamide; N-(3-(4-chlorophenoxy)phenyl)-4-(difluoromethyl)- 1 ,2,3-thiadiazole-5- carboxamide; 4-(difluoromethyl)-N-(3-phenoxyphenyl)-l.,2,3-thiadiazole-5-carboxamide; N-(3- (3,4-dichlorophenoxy)phenyl)-4-(difluoromediyl)- l,2,3-thiadiazOle-5-carboxamide; 4- (diiluoromethyl)-N'-phenyl- 1 ,2,3-thiadiazole-5-carbohydrazide N'-(4-chlorophenyl)-4- (difluorometliyl)- l,2,3-thiadiazole-5-carbohydrazide 4-(chloromethyl)-N-(3- ((trifluoromet yl)thio)phenyl)-l,2,3-thia.diazole-5-carboxaniide; 4-(thiocyanatomet yl)-N-(4- (trifkioromethoxy)phenyl)- l,2,3"thiadiazole-5-carboxamide; N-(4-fluoro-3- (trifliioromethyi)phenyi)-4-(to 4- (thiocyanatomethyl)-N-(3-((trifluoromethyl)thio)phenyl)- l,2,3-thiadiazole-5-carboxan^ 4- (thiocyanatomethyl)-N-(4-((trifluorometh^ (4- (difluoromethyl)- 1 ,2,3-thiadia ol-5-yl)(3,4-dihydroisoquinolin-2(lH)-yl)methanone; 4- (difluoromethyl)-N-methyl-N-(4-((trifl^
carboxamide; 4-(difluoroniethyl)-N-methyl-N-(4-((trifluoromethyl)sul inyl)phenyl)- 1 ,2,3- thiadiazole-5-carboxamide; N'-(3,4-dichlorophenyl)-4-(difluoromethyl)- l,2,3-tliiadiazole-5- carbohydrazide 4-(diftuoromethyl)-N-(3-((dffi^
carboxamide; 4-(difluoromethyl)-N-(3-((trifluoromethyl)thio)phenyl)-l,2,3-thiadiazole-5- carboximidamide 4-(difluoromethyl)-N-(3-(trifluoromethyl)phenyl)- l,2,3-thiadiazole-5- carboximidamide 4-(difluoiOmethyl)-N-(3-(pentafluoro-16-sulfaneyl)phenyl)-l ,2,3-thiadiazole-5- carboximidamide 4-(difluoromethyl)-N-(3-fluorophenyl)-l,2,3-thiadiazole-5-carboxirrddarrdde N-(3-broniophenyl)-4-(ditluoromethyl)-l,2,3-thiadiazole-5-carboxiniidamide N-([ Ι ,Γ-bi phenyl] - 4-yl)-4-(difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(4-cyanophenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(4-bromo-2-(trifluoromethyl)phenyl)-4- (morpholinomethyl)-l,2,3-thiadiazole-5-carboxamide; 4-(morpholinomethyl)-N-(3-(pentafluoro- 16-sulfaneyl)phenyl)- 1 ,2,3-thiadiazole-5-earboxamide; ethyl 4-(4-(difluoromethyl)- 1 ,2,3- thiadiaz.ole-5-carboxamido)benzoate ethyl 3 -(4-(difluoromethyl)- 1 ,2,3 -thiadiazole-5- carboxamido)benzoate N-(3-(pentafluoro-16-sulfaneyl)phenyl)-4-(thiocyanatomethyl)- 1,2,3- thiadiazole-5-carboxamide; 4-(thiocyanatomethyl)-N-(3-(trifluoromethoxy)phenyl)- 1,2,3- thiadiazole-5-carboxaniide; N-(4-(difl.uoromethoxy)phenyl)-4-(thiocyanatomethyl)- 1,2,3- thiadiazole-5-carboxamide; N-(3-(difluoromethoxy)phenyl)-4-(thiocyanatomethyl)- 1,2,3- thiadiazole-5-carboxamide; 4-(thiocyanatomethyl)-N-(3-(trifluoromethyl)phenyl)- 1,2,3- thiadiazole-5-carboxamide; 4-(chloromethyl)-N-(3-(difluorometlioxy)phenyl)- l,2,3-thiadiazole- 5-carboxamide; 4-(chlorome(hyl)-N-(4-(difluoromethoxy)phenyl)-l,2,3-thiadiazole-5- carboxamide; 4-((4-niethylpiperazin-l-yl)meA
thiadiaz.ole-5-carboxamide; 4-((4-methylpiperazin-l-yl)methyl)-N-(3-((rifluoromethoxy)phenyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4-((4-methylpiperazin- 1 -yl)methyl)-N-(4- ((rifluoromethoxy)phenyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4-((4-methylpiperazin- 1- yl)methyl)-N-(4-((trifluoro^ N-(4-fluoro-3-
(trifliiorGmethyl)phenyl)-4-((4-m
N-(4-chlorophenyl)-4-((4-methylpiperazin-l-yl)m 4-((4- methylpiperazin-l-yl)methyl)-N-(3-(pentafluoro-16-sulfaneyl)phenyl)-l,2,3-tliiadiazole-5- carboxamide; N-(3 4'-difluoro-[l, -biphenyl]-2-yl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carboxamide; 4-(difluoromethyl)-N-(thiazol-2-yl)- l,2,3-thiadiazole-5-carboxainide; 4- (difluoromelhyl)-N-(lH-pyrazol-3-yl)-l,2,3-thiadiazole-5-carboxamide; N-(benzo[d]thiazol-2- yl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(pyridazin-4-yl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(3-(trifluoromethoxy)phenyl)-4-(trifluoromethyl)- 1 ,2,3- thiadiazole-5-carbothioamide; N-(2-chloro-4-((trifluoromethyl)thio)phenyl)-4-(trifl.uoromethyl)- l,2,3-thiadiazole-5-carbothioamide; N-(2-chloro-4-(trifluoromethoxy)phenyl)-4- (triiluoroniethyl)-l,2,3-thiadiazole-5-carbothioamide; N-(4-(trifluoromethoxy)phenyl)-4- (trifluoromethyl)- l,2,3-thiadiazole-5-carbothioamide; 4-(trifluoromethyl)-N-(3- (( fl.uoromethyl)thio)phenyl)-l,2,3-thi diazole-5-caxbothioamide; N-(2-cyclopropyl-4- (trifluoromethoxy)phenyl)-4-(trifluoromethyl)- 1 ,2,3-thiadiazole-5-carbothioamide; N-(4- cMorophenyl)-4-(trifluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; 4-(trifluoromethyl)-N-(3- (trifluoromethyl)phenyl)- l,2,3-thiadiazole-5-carbothioamide; N-(3-chlorophenyl)-4- (t3ifluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; 4-(fluoromethyl)-N-(4-methoxybenzyl)-N- methyl- 1 ,2,3-thiadiazole-5-carboxamide; N-(3',4'-difluoro-[l,r-biphenyl]-2-yl)-4-methyl- 1,2,3- thiadiaz.ole-5-carbothioamide; 4-(difluoromethyl)-N-(5-(trifluoromethyl)-l,3,4-thiadiazol-2-yl)- l,2,3-thiadiazole-5-carboxamide; 4-(morpholinomethyl)-N-(4-(trifluoromethyl)phenyl)- 1,2,3- thiadiazole-5-carboxamide; N-(3-chlorophenyl)-4-(thiomorpholinomethyl)-l,2,3-thiadiazole-5- carboxami.de; 4-(Λΐο^ο ηοΗηο^εΛν1)-^
5-carboxamide; 4-(miomorpholinomethyl)-N-(3-(trifluoromethyl)phenyl)-l,2,3-thiadiazole-5- carboxamide; N-(2-chloro-4-(trifluoromethyl.)phenyl)-4-(thiomorpholinomethyl)- 1 ,2,3- diiadiazole-5-carboxamide; 4-(difluoromethyl) -N-(2- ((3E,5E,6E)-5-(methoxyimino) -4,6- dimemyl-2,8-dioxa-3,7-diazanona-3,6-dien-l-yl)phenyl)-l ,2,3-thiadiazole-5-carboxamide; N- (2,2-difluorobenzo[d] [ 1 ,3]dioxol-5-yl)-4-(difluoromethyl)- 1 ,2,3 -thiadiazole-5-carboxamide; 4- (diiluoromethyl)-N-hydroxy- 1 ,2,3-thiadiazole-5-carboximidamide N-(4-chlorophenyl)-4- (fluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(2-chloro-4-(trifluoromethyl)plienyl)-4- (fluoromethyl)- 1,2, 3-ihiadiazole-5-carboxami.de; 4-(fluoromethyl)-N-(3-(pentafluoro-16- sulfaneyl)phenyl)-l,2,3-thiadiazole-5-carboxaniide; N-(3-chlorophenyl)-4- (((trifluoromethyl)thio)methyl)-l,2,3-thiadiazole-5-carboxainide; N-(3-(trifluoromethyl)phenyl)- 4-(((tri.fluoromethyl)thio)methyl)-l ,2,3-thiadiazole-5-carboxaniide; N-(4-chlorophenyl.)-4- (((trifluoromethyl)thio)methyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4- (((tri†luoromeihyl)thio)m
carboxamide; 4-(((trifluoromet yl)thio)methyl)-N-(3-(((rifluoromethyl)thio)phenyl)- 1,2,3-
{hiadiazole-5-carboxami.de; N-(4-(trifluoromethoxy)phenyl)-4-(((trifluoromethyl)thio)methyl)- 1 ,2,3 -thiadiazole-5-carboxamide; N-(3-(trifluoromethoxy)phenyl)-4- (((trifluoromet yl)thio)methyl)-l,2,3-thiadiazole-5-carboxamide; N-(2,4-dichlorophenyl)-4- (fluoromethyl)- l,2,3-thiadiazole-5-carboxamide; N-(2-fluoro-3-(trifluoromethyl)phenyl)-4- (fluoromethyl)-l,2,3-thiadiazole-5-carboxamide; 4-(fluoromethyl)-N-(2- (trifluoromethyl)phenyl)- l,2,3-thiadiazole-5-carboxamide; N-(2-chloro-3- (trifluoromethyl)phenyl)-4-(fluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(4- ( fl.uoromethyl)phenyl)-4-(((tiifluorom N- (2-c oro-4-((rifluoromethyl)phenyl)-4-(((trifluoromethyl)thio)methyl)-l,2,3-^
carboxamide; 4-(fluoromethyl)-N-(3-(trifluoromethoxy)phenyl)-l ,2,3-thiadiazole-5- carboxamide; 4-(fluoiOmethyl)-N-(4-(trifluoromethoxy)phenyl)-l,2,3-thiadiazole-5- carboxamide; N-(4-c loro-2-fluorophenyl)-4-(f!uorometiiyl)-l,2,3-thiadiazole-5-carboxamide; N-(4-chlorophenyl)-4-(((trifluoromethyl)sulfmy N- (3-(trifluorometiiyl)phenyl)-4-(((tri^
carboxamide; N-(3-cyclopropyl-5-methylphenyl)-4-(difluoiOmethyl)- l,2,3-tliiadiazole-5- carboxamide; N-(3-cyclopropylphenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N- (3,5-dimethylphenyl)-4-(fl.uoromethyl)-l,2,3-thiadiazole-5-caxboxamide; N-(3- (cyclopropylethynyl)phenyl)-4-(difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4- (difluorometliyl)-N-(o-tolyl)-l,2,3-tliiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(m-tolyl)- l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(5-fluoro-2-methylphenyl)- 1,2,3- thiadiaz.ole-5-carboxamide; N-(5-chloro-2-methylphenyl)-4-(difl.uoromethyl)-l,2,3-thiadiazole-
5-carboxamide; 4-(difluoromethyl)-N-(2-iodo-5-methylphenyl)-l,2,3-thiadiazole-5- carboxamide; 4-(difluoroniethyl)-N-(2-meihyl-5-(tfifluoromethyl)
carboxamide; 4-(difluoromethyl)-N-(4-methyl-3-( fluoromethyl)phenyl)-l,2,3-thiadiazole-5- carboxamide; 4-(difiuoromethyI)-N-(4-iluoro-3-m
4-(difluoromethyl)-N-(3-fluoro-4-methylphenyl)- l,2,3-tliiadiazole-5-carboxamide; N-(4-bromo- 2,5-dimethylphenyl)-4-(difluoromethyl)-l,2,3-(hiadiazole-5-carboxaniide; N-(4-bromo-2-fluoro- 5-metliylphenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(4-bromo-2-chloro-5- met ylphenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxaniide; N-(3-fluoro-5- methylphenyl)-4-(trifluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; N-(3,5-dichlorophenyl)- 4-(trifluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; N-(3-chloro-5-methylphenyl)-4- (trifluorornethyl)-l,2,3-thiadiazole-5-carbothioaniide; N-(3-bromo-5-methylphenyl)-4- (difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3-fluoro-5- methylphenyl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(3-chloro-5-methylphenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(4-(trifluoromethoxy)phenyl)-4- (((trifluoromethyl)sulfinyl)methyl)-l ,2,3-(hiadiazole-5-carboxamide; 4-(difluoromet yl)-N-(3,5- dimethylphenyl)-l,2,3-tliiadiazole-5-carboxamide; N-(3-(trifluoromethoxy)phenyl)-4- (((trifluoromet yl)sulfinyl)methyl)-l,2,3-thiadiazole-5-carboxamide; N-(3,5- dicyclopropylphenyl)-4-(difluoiOmetliyl)-l,2,3-tliiadiazole-5-carboxamide; 4-(difluoromethyl)- N-(3-fluoro-5-methylphenyl)-l,2,3-thiadiazole-5-carbothioamide; N-(3-bromo-5-methylphenyl)- 4-(difluoromethyl)-l,2,3-thiadiazole-5-cai"bothioamide; 4-(difluoromethyl)-N-(3,5- dimethylphenyl)-l,2,3-thiadiazole-5-carbothioamide; N-(3-chloro-5-methylphenyl)-4- (difluoromethyl)- 1 ,2,3-thiadiazole-5-carbothioamide; N-(3-chloro-5-methylphenyl)-4- (difluoromethyl)-N-methyl-l,2,3-thiadiazole-5-carboxarnide; N-(3-bromo-5-methylphenyl)-4- (difluoromethyl)-N-methyl-l,2,3-thiadiazole-5-carboxamide; 4-(difl.uoromethyl)-N-(3,5- dimethylphenyl)-N-methyl- l,2,3-miadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3-fluoro-5- methylphenyl)-N-methyl-l ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2,5- dimethylphenyl)-l,2,3-thiadiazole-5-cai"boxamide; N-(2-bromo-5-metliylphenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(3-aminophenyl)-4-(difluoromethyl)- 1 ,2,3- thiadiazole-5-carboxamide; N-(3-cyclopropylphenyl)-4-(fluoromethyl)-l,2,3-thiadiazole-5- carboxamide; N-(3-bromophenyl)-4-(fluoromethyl)-l,2,3-thiadiazole-5-carboxamide; 4- (fluoromethyl)-N-(4-methoxybenzyl)-l,2,3-thiadiazole-5-carboxamide; N-(2-chloro-5- methylphenyl)-4-(difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2- fluoro-5-methylphenyl)-l ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(5,6,7,8- tetrahydronaphthalen- 1-yl)- 1 ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-( 1 ,2,3 ,4- tetrahydronaphthalen-l-yl)-l,2,3-thiadiazole-5-carboxarnide; N-(2-bromo-4-methylphenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(2-chloro-5-methoxyphenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carboxaniide; N-(3-chloro-2-methylphenyl)-4- (difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4-(dif luoromemyl)-N-(2,3-dihydro- lH-inden- 4-yl)-l,2,3-thiadiazole-5-carboxaniide; N-(4-chloro-3-(difluoromethyl)phenyl)-4- (chloromethyl)- 1 ,2,3 -thiadiazole-5-carboxamide; N-(4-chloro-3-(difluoromethyl)phenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; N-(4-chloro-3-(difluoromethyl)phenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(4-chloro-3-(difluoromethyl)phenyl)-4- (difluoromethyl)-N-methyl-l,2,3-thiadiazole-5-carboxamide; N-(3-cyclopropyl-5- methylphenyl)-4-(difl.uoromethyl)-l,2,3-thiadiazole-5-carbothioamide; N-(4-chloro-3- (difluoromethyl)phenyl)-4-(((trifluoromethyl)thio)methyl)-l,2,3-thiadiazole-5^ 4- (difluoromethyl)-N-methyl-N-(5,6,7,8-tetrahydronaphthalen-l-yl)-l ,2,3-thiadi^^
carboxamide; 4-(difluoromethyl)-N-(5-fluoro-2-methylphenyl)-N-methyl- 1 ,2,3-thiadiazole-5- carboxamide; N-(5-chloro-2-methylphenyl)-4-(difluoromethyl)-N-methyl-l,2,3-thiadiazole-5- carboxamide; 4-(difluoromethyl)-N-(2,5-dimethylphenyl)-N-methyl-l,2,3-thiadiazole-5- carboxamide; 4-(difluoromethyl)-N-methyl-N-(o-tolyl)-l,2,3-thiadiazole-5-carboxa.mide; 4- (difluoromethyl)-N-mediyl-N-(2-methyl-5-(trifluorometliyl)phenyl)-l,2,3-tliiadiazole-5- carboxamide; 4-(difluoromethyl)-N-(2-fluoro-5-methylphenyl)-N-methyl-l,2,3-thiadiazole-5- carboxamide; N-(3-chloro-2- methylphenyl)-4-(difluorometliyl)-N- methyl- l,2,3-thiadiazole-5- carboxamide; N-(2-bromo-4-methylphenyl)-4-(difluoromethyl)-N-methyl-l,2,3-thiadiazole-5- carboxamide; 4-(difluoromethyl)-N-(2-methoxyphenyl)- l,2,3-thiadiazole-5-carboxamide; 4- (difluoromemyl)-N-(2-methoxy-5-methylphenyl)-l,2,3-miadiazole-5-carboxamide; N-(4- brornonaphthalen-l -yl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)- N-(3-isopropoxyphenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(6- methylpyridin-2-yl)-l,2,3-thiadiazole-5-carboxaniide; 4-(difluoromethyl)-N-(3-fluoro-4- methylphenyl)-N-methyl-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-methyl-N-(4- methyl-3-(trifluoromethyl)phenyl)-l,2,3-thiadiazole-5-carboxaiTiide; 4-(difluoromethyl)-N-(4- fluoiO-3-methylphenyl)-N-metliyl-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3- isopropoxyphenyl)-N-methyl-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2- methoxy-5-methylphenyl)-N-metliyl-l,2,3-thiadiazole-5-carboxamide; N-(4-bromonaphthalen-l - yl)-4-(difluoromethyl)-N-me(hyl-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2- methoxyphenyl)-N-raethyl-l,23-thiadiazole-5-carboxamide; N-(4-bromo-2,5-dimethylphenyl)- 4-(difluoromethyl)-N-methyl- 1 ,2,3-thiadiazole-5-carboxamide; N-(4-chloro-3- (fluoromediyl)phenyl)-4-(difluoromediyl)-l,2,3-thiadiazole-5-carboxamide; N-(2-bromo-4- chloro-5-(difluoromediyl)phenyl)-4-(trifluoro N-(2- bromo-4-chloro-5-(difluoromethyl)phenyl)-4-(difluoromethyl)-l ,2,3-thiadiazole-5- 4-(difluoromethyl)-N-(2,6-dimethylphenyl)-l,2,3-tMadiazole-5-carboxamide; N-(4-bromo-3- methylphenyl)-4-(difluoromethyl)-l.,2,3-thiadiazole-5-carboxamide; 4-(chloromethyl)-N-(3,5- dimethylphenyl)-l,2,3-tliiadiazole-5-carboxamide; 4-(chloromethyl)-N-(3-fluoro-5- methylphenyl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(3-chloro-5-methylphenyl)-4- (chloromethyl)- 1 ,2,3 -thiadiazole-5-carboxamide; 4-(chloromethyl)-N-(3,5-dichlorophenyl)- l,2,3-thiadiazole-5-carboxamide; 4-(chloromethyl)-N-(3,5-difluorophenyl)-l,2,3-thiadiazole-5- carboxaniide; N-(3 -chloro-5-methylphenyl)-4-methyl- 1 ,2,3-t adiazole-5-carbothioamide; N-(3- fluoro-5-methylphenyl)-4-methyl-l,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(2- ethylphenyl)-l ,2,3-thiadiazole-5-carboxamide; 7-bromo-5-(3-(trifl.uoromethyl)phenyl)- [l,2,3]thiadiazolo[5,4-c]pyridin-4(5H)-one; 4-(difluoromethyl)-N-(2-fluoro-5- (trifluorornethyl)phenyl)-N-methyl-l,2,3-thiadiazole-5-carboxamide; 4-(chloromethyl)-N-(2- ethylphenyl)-l,2,3-tWadiazole-5-carboxamide; N-(2-bromo-4-chloro-3-(difluoromethyl)phenyl)- 4-(difluoromethyl)-l.,2,3-thiadiazole-5-carboxamide; N,N-dicyclohexyl-4-(difl.uoromethyl)- l,2,3-thiadiazole-5-carboxamide; N-(3,5-dichlorophenyl)-4-(((trifluoromethyl)thio)methyl)- l,2,3-thiadiazole-5-carboxamide; N-(3-chloro-5-methylphenyl)-4- (((trifluoromethyl)thio)metliyl)-l,2,3-tliiadiazole-5-cai"boxamide; N-(3-bromo-5-methylphenyl)- 4-(((tTifluoromethyl)thio)methyl)-l,2,3-thiadiazole-5-carboxamide; N-(3-fluoro-5- methylphenyl)-4-(((trifluoromediyl)thio)methyl)-l ,2,3-thiadiazole-5-carbox N-(3,5- dimethylphenyl)-4-(((trifluoromethyl)^ 4- (difluorometliyl)-N-(2-fluorobenzyl)-N-metliyl-l,2,3-thiadiazole-5-carboxamide; 4- (dMuoromethyl)-N-(5-methylpyridin-2-yl)- 1 ,2,3-tMadiazole-5-carboxamide; N-(4-chloro-3- (difluoroniethyl)phenyl)-4-(fluoromethyl)-l ,2,3-thiadiazole-5-carboxamide; 4-(difl.uoromethyl)- N-(2,6-dimethylphenyl)-N-methyl-l,2,3-thiadiazole-5-carboxamide; N-(4-bromo-3- methylphenyl)-4-(difluoromethyl)-N-methyl-1.,2,3-thiadiazole-5-carboxamide; 4-(chloromethyl)- N-(3 ,5 -dichlorophenyl) - -methyl- 1 ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl) -N-(4- ethylthiazol-2-yl)-l ,2,3-thiadiazole-5-carboxamide; N-(4'-chloro-5-methyl-[ l,r-biphenyl]-3-yl)- 4-(difluoromethyl)-l,2,3-diiadiazole-5-carboxamide; N-(3',4'-dichloro-5-methyl-[l,r-biphenyl]- 3-yl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; 5-(4-chlorophenyl)-4,5-dihydro-6H- pyrrolo[3,4-d][l,2,3]thiadiazol-6-one; 5-(4-(trifluorometiioxy)phenyl)-4,5-dihydro-6H- pyrrolo[3,4-d][l,2,3]thiadiazol-6-one; 5-(3-(t"rifluoromethoxy)phenyl)-4,5-dihydro-6H- pyrrolo[3,4-d] l ,2,3]thiadiazol-6-one; 5-(3-((trifl.uoromethyl)thio)phenyl)-4,5-dihydro-6H- pyrrolo[3,4-d][l,2,3]thiadiazol-6-one; 5-(4-((trifluoromethyl)thio)phenyl)-4,5-dihydro-6H- pyrrolo[3,4-d][l,2,3]thiadiazol-6-one; 5-(3-chlorophenyl)-4,5-di ydro-6H-pynOlo[3,4- d][l,2,3]thiadiazol-6-one; 5-(3-(trifluoromethyl)phenyl)-4,5-diriydro-6H-pyrrolo[3,4- d][ l,2,3]thiadiazol-6-one; 5-(4-((difluoromethyl)thio)phenyl)-4,5-dihydro-6H-pyrrol.o[3,4- d][l,2,3]thiadiazol-6-one; 5-(3,5-dichlorophenyl)-4,5-di ydro-6H-pyrrolo[3,4- d] [l.,2,3]thiadiazol-6-one; 5-(3-(trifluoromethoxy)phenyl)-6,7-dihydro- l ,2,3]thiadiazolo[5,4- c]pyridin-4(5H)-one; 5-(3-(trifluoromethyl)phenyl)-6,7-dihydro-[l,2,3]thiadiazolo[5,4-c]pyiidm^ 4(5H)-one; 5-{3-(pentafluoro 6-surfaneyl)phen^
4(5H)-one; 5-(4-( fluoromelhyl)phenyl)-6,7-di ydro-[l,2,3]thiadiazolo[5,4-c]pyridin-4(5H)- one; 7-bromo-[l,2,3]t iadiazolo[5,4-c]pyridin-4(5H)-one; 5-(4-(trifluoromethyl)phenyl)- [ 1 ,2,3]thiadiazolo[5,4-c]pyridin-4(5H)-one; 5-(3-( 1 , 1 ,2,2-tetrafluoroethoxy)phenyl)-6,7-dihydro- [l,2,3]thiadiazolo[5,4-c]pyridin-4(5H)-one; 4-(difluoromet yl)-N-methyl-N-(2- (trifl.uoromethyl)benzyl)- l,2,3-thiadiazole-5-carboxaniide; 4-(difluoromethyl)-N-(3- fluorobenzyl)-N-methyl-l,2,3-thiadiazole-5-carboxamide; N-(2-chlorobenzyl)-4- (difluoromethyl)-N-methyl- 1 ,2,3-thiadiazole-5-carboxamide; N-(3 ,5-difluorobenzyl)-4- (difluoromethyl)-N-methyl- 1 ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2,5- dimethylbenzyl)-N-methyl-l,2,3-thiadiazole-5-carboxaiTiide; 4-(difluoromethyl)-N-(3- ((trifluoromethyl)thio)phen^ 4-(difluoromethyl)-N-(3- ( fluoromethyl)phenyl)-l,2,3-thiadiazole-5-carboxirrddamide; 4-(difluoromethyl)-N-(3- (pentafluoro-16-sulfaneyl)phenyl)- 1 ,2,3 -t adiazole-5-carboximidamide; 4-(difluoromethyl)-N- (3-fluorophenyl)-l,2,3-thiadiazole-5-carboximidamide; N-(3-bromophenyl)-4-(dif uoromethyl)- l,2,3-thiadiazole-5-carboximidamide;
Any of the compounds according to the invention can exist in one or more optical, geometric or chiral isomer forms depending on the number of asymmetric centres in the compound, The invention thus relates equally to all the optical isomers and to their racemic or scalemic mixtures (the term "scalemic" denotes a mixture of enantiomers in different proportions), and to the mixtures of all the possible stereoisomers, in all proportions. The diastereoisomers and/or the optical isomers can be separated according to the methods which are known per se by a person ordinary skilled in the art.
Any of the compounds according to the invention can also exist in one or more geometric isomer forms depending on the number of double bonds in the compound. The invention thus relates equally to ail geometric isomers and to all possible mixtures, in all proportions. The geometric isomers can be separated according to general methods, which are known per se by a person ordinary skilled in the ait. Any of the compounds according to the invention, can also exist in one or more amorphic or isomorphic or polymorphic forms, depending on their preparation, purification storage and various other influencing factors. The invention thus relates all the possible amorphic, isomorphic and polymorphic forms, in all proportions. The amorphic, isomorphic and polymorphic forms can be prepared and/or separated and/or purified according to general methods, which are known per se by a person ordinary skilled in the art.
The definitions of the substituents given herein, are specified by their conventional chemical formulae or name, written from left to right, they equally encompass the chemically identical substituents that would result from writing the structure from right to left. The definitions given herein are for illustration purpose only and do not construe the scope of the invention.
As used herein, the terms "comprises", "comprising", "includes", "including", "has", "having", "contains", "containing", "characterized by" or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated. For example, a composition, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method. The transitional phrase "consisting of excludes any element, step or ingredient not specified. If in the claim, such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase "consisting of appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause: other elements are not excluded from the claim as a whole.
The transitional phrase "consisting essentially of" is used to define a composition or method that includes materials, steps, features, components or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components or elements do not materially affect the basic and novel characteristic(s) of the claimed invention. The term "consisting essentially of occupies a middle ground between "comprising" and "consisting of.
Further, unless expressly stated to the contrary, "or" refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present). Also, the indefinite articles "a" and "an" preceding an element or component of the present invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore "a" or "an" should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular.
As referred to in this disclosure, the term "invertebrate pest" includes arthropods, gastropods and nematodes of economic importance as pests. The term "arthropod" includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs and symphylans. The term "gastropod" includes snails, slugs and other Stylommatophora. The term "nematode" refers to a living organism of the Phylum Nematoda. The term "helminths" includes roundworms, heartworms, phytophagous nematodes (Nematoda), flukes (Tematoda), acanthocephala and tapeworms (Cestoda).
In the context of this disclosure "invertebrate pest control" means inhibition of invertebrate pest development (including mortality, feeding reduction, and/or mating disruption), and related expressions are defined analogously. The term "agronomic" or "agriculturally" refers to the production of field crops such as for food and fiber and includes the growth of corn, soybeans and other legumes, rice, cereal (e.g., wheat, oats, barley, rye, rice, maize), leafy vegetables (e.g., lettuce, cabbage, and other cole crops), fruiting vegetables (e.g., tomatoes, pepper, eggplant, crucifers and cucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g., pome, stone and citrus), small fruit (berries, cherries) and other specialty crops (e.g., canola, sunflower, olives).
The term "nonagronomic" refers to other than field crops, such as horticultural crops (e.g., greenhouse, nursery or ornamental plants not grown in a field), residential, agricultural, commercial and industrial structures, turf (e.g., sod farm, pasture, golf course, lawn, sports field, etc.), wood products, stored product, agro-forestry and vegetation management, public health (i.e. human) and animal health (e.g., domesticated animals such as pets, livestock and poultry, undomesticated animals such as wildlife) applications.
Nonagronomic applications include protecting an animal from an invertebrate parasitic pest by administering a parasiticidally effeciive (i.e. biologically effective) amount of a compound of the present invention, typically in the form of a composition formulated for veterinary use, to the animal to be protected. As referred to in the present disclosure and claims, the terms "parasiticidal" and "parasiticidally" refers to observable effects on an invertebrate parasite pest to provide protection of an animal from the pest. Parasiticidal effects typically relate to diminishing the occurrence or activity of the target invertebrate parasitic pest. Such effects on the pest include necrosis, death, retarded growth, diminished mobility or lessened ability to remain on or in the host animal, reduced feeding and inhibition of reproduction. These effects on invertebrate parasite pests provide control (including prevention, reduction or elimination) of parasitic infestation or infection of the animal. Compounds of the present disclosure may be present either in pure form or as mixtures of different possible isomeric forms such as stereoisomers or constitutional isomers. The various stereoisomers include enantiomers, diastereomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, polymorphs, and geometric isomers. Any desired mixtures of these isomers fall within the scope of the claims of the present disclosure. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other isomer(s) or when separated from the other isomer(s). Additionally, the person skilled in the art knows processes or methods or technology to separate, enrich, and/or to selectively prepare said isomers. The meaning of various terms used in the description shall now be illustrated.
The term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl" or - N(alkyl) or alkyicarbonyialkyl or alkylsuphonylamino includes straight -chain or branched Q to C24 alkyl, preferably Cj to C 15 alkyl, more preferably C\ to C10 alkyl, most preferably Cj to C6 alkyl. Representative examples of alkyl include methyl, ethyl, propyl, 1-methyiethyl, butyl, 1 - methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3- methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyi, 1 ,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2- dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1- ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1 -ethyl- 1 -methylpropyl and l-ethyl-2-methylpropyl or the different isomers. If the alkyl is at the end of a composite substituent, as, for example, in alkylcycloalkyl, the part of the composite substituent at the start, for example the cycloalkyl, may be mono- or polysubstituted identically or differently and independently by alkyl. The same also applies to composite substituents in which other radicals, for example alkenyl, alkynyl, hydroxyl, halogen, carbonyl, carbonyloxy and the like, are at the end.
The term "Alkenyl", used either alone or in compound words includes straight-chain or branched Ci to C24 alkenes, preferably C\ to C15 alkenes, more preferably C-, to C10 alkenes, most preferably Ci to C6 alkenes. Representative examples of alkenes include ethenyl, 1 -propenyl, 2- propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1 -methyl- 1 -propenyl, 2-methyl-l- propenyl, l-methyl-2 -propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4- pentenyl, 1 -methyl- 1-butenyl, 2-metliyl- 1-butenyl, 3 -methyl- 1-butenyl, l-methyl-2-butenyl, 2- methyl-2-butenyl, 3-methyl-2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3- butenyl, l,l-dimethyl-2-propenyl, 1,2-dimethyl-l -propenyl, l,2-dimethyl-2 -propenyl, 1 -ethyl- 1- propenyl, l-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-mefhyl-
1- pentenyl, 2-methyl- 1 -pentenyl, 3-methyl-l-pentenyl, 4-niethyl- 1 -pentenyl, l -methyl-2- pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, l-methyl-3-pentenyl,
2- methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1 -methyl-4-pentenyl, 2-methyl- 4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, l,l-dimethyl-2-butenyl, l,l-dimethyl-3- butenyl, 1,2-dimethyl-l-butenyl, l,2-dimethyl-2-butenyl, 1 ,2-dimethyl-3-butenyl, 1,3-dimethyl- 1 -butenyl, l,3-dimethyl-2-butenyl, i,3-dimemyi-3-butenyi, 2,2-dimethy 1-3 -butenyl, 2,3-dimethyl- 1 -butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-l-butenyl, 3,3- dimethyl- 2- butenyl, 1 -ethyl- 1-butenyl, l-ethyl-2-butenyl, l-ethyl-3-butenyl, 2-ethyl- 1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, l,l,2-trimethyl-2-propenyl, l-ethyl-l-methyl-2-propenyl, 1- ethyl-2-methyl-l-propenyl and l-ethyl-2-methyl-2-propenyl and the different isomers. "Alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. This definition also applies to alkenyl as a part of a composite substituent, for example haloalkenvl and the like, unless defined specifically elsewhere.
Representative examples of alkynes include ethynyl, 1 -propynyl, 2-propynyl, 1-butynyl, 2- butynyl, 3-butynyl, l-methyl-2 -propynyl, 1-pentynyl, 2-pentynyi, 3-pentynyl, 4-pentynyl, 1- methyl-2-butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-l-butynyl, 1 , l-dimethyi-2- propynyl, 1 -ethyl -2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1- methyl-2-pentynyl, l-methyl-3-pentynyl, l-methyl-4-pentynyl, 2 -methyl -3-pentynyl, 2-methyl-4- pentynyl, 3-methyl-l-pentynyl, 3-methyl-4-pentynyl, 4-methyl-l-pentynyl, 4-methyl-2-pentynyl,
1 , 1 -dimethyl -2-butynyl, l,l-dimethyl-3-butynyl, 1,2-dimethyl- 3-butynyl, 2,2-dimethyl-3-butynyl,
3,3-dimethyl-l-butynyl, l-ethyl-2-butynyl, l-ethyl-3-butynyl, 2-ethyl-3-butynyl and l-ethyl-l- methyl-2-propynyl and the different isomers. This definition also applies to alkynyl as a part of a composite substituent, for example haloalkynyl etc., unless specifically defined elsewhere. "Alkynyl" can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. Cycloalkyl means alkyl closed to form a ring. Representative examples include but are not limited to cyclopropyl, cyclopeiityi and cyclohexyl. This definition also applies to cycloalkyl as a part of a composite substituent, for example cycloalkylalkyl etc., unless specifically defined elsewhere.
Cycloalkenyl means alkenyl closed to form a ring including monocyclic, partially unsaturated hydrocarbyl groups. Representative examples include but are not limited to cyclopropenyl, cyclopentenyl and cyclohexenyl. This definition also applies to cycloalkenyl as a part of a composite substituent, for example cycloalkenyialkyl etc., unless specifically defined elsewhere. Cycloalkynyl means alkynyl closed to form a ring including monocyclic, partially unsaturated groups. Representative examples include but are not limited to cyclopropynyl, cyclopentynyl and cyclohexynyl. This definition also applies to cycloalkynyl as a part of a composite substituent, for example cycloalkynylalkyl etc., unless specifically defined elsewhere.
Cycloalkoxy, cycloalkenyloxy and the like are defined analogously. Non limiting examples of cycloalkoxy include cyclopropyioxy, cyclopentyloxy and cyclohexyloxy. This definition also applies to cycloalkoxy as a part of a composite substituent, for example cycloalkoxy alkyl etc., unless specifically defined elsewhere.
The term "halogen", either alone or in compound words such as "haioalkyl" or "halogenoalkyl", includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haioalkyl" or "halogenoalkyl", said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of "haioalkyl" include chloromethyl, bromomethyl, dichloromethyl, trichloromethyi, fluoromethyl, difluoromethyl, trifluoromethyi, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-irifluoroethyl, 2-chloro-2-fluoroethyl, 2- chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 1,1- dichl.oro-2,2,2-trifluoroethyl, and l,l ,l-trifluoroprop-2-yl. This definition also applies to haioalkyl as a part of a composite substituent, for example haloalkylarninoalkyl etc., unless specifically defined elsewhere.
The terms "haloalkenyl" or "halogenoalkenyl", "haloalkynyl" or "halogenoalkynyl" are defined analogously except that, instead of alkyl groups, alkenyl and alkynyl groups are present as a part of the substituent.
The term "haloalkoxy" or "halogenoalkoy" means straight-chain or branched alkoxy groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above. Non-limiting examples of haloalkoxy include chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1- bromoethoxy, 1 -fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroetlioxy, 2- chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2- trichloroethoxy, pentafluoroethoxy and l,l,l-trifluoroprop-2-oxy. This definition also applies to haloalkoxy as a part of a composite substituent, for example haloalkoxyalkyl etc., unless specifically defined elsewhere.
The term "haloalkylthio" or "haloalkylsufanyl" or "halogenoalkylsulfanyl" means straight-chain or branched alkylthio groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above. Non-limiting examples of haloalkylthio include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1- fluoroethylthio, 2- fluoroethylthio, 2,2-difiuoroethyithio, 2,2,2-tri.fluoroethylthio, 2-chloro-2- fluoroethylthio, 2- chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2 -trichloroet ylthio, pentafluoroethylthio and l.,l,l-trifl.uoroprop-2-ylthio. This definition also applies to haloalkylthio as a part of a composite substituent, for example haloalkylthioalkyl etc., unless specifically defined elsewhere.
Examples of "haloalkylsulfinyl" include CF3S(G), CC13S(G), CF3CH2S(G) and CF3CF2S(0). Examples of "haloalkylsulfonyl" include CF3S(0)2, CC13S(0)2, CF3CH2S(0)2 and CF3CF2S(0)2. Hydroxy means -OH, Amino means -N(R)2, wherein R can be H or any possible substituent such as alkyl, Carbonyl means -C(O)- , carbonyl oxy means -QC(Q)~, sulfinyl means SO, sulfonyl means S(0)2.
The term "Alkoxy" used either alone or in compound words included Cj to C24 alkoxy, preferably Ci to Qs alkoxy, more preferably Ci to C10 alkoxy, most preferably C. to C alkoxy. Examples of alkoxy include methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1- methylpropoxy, 2-methylpropoxy, 1 , 1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2- methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1,1- dimethylpropoxy, 1 ,2-dimethylpropoxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, L l-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2- dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1 -et ylbutoxy, 2-ethylbutoxy, 1,1 ,2- trimethylpropoxy, 1,2,2-trimethylpropoxy, 1 -ethyl- 1 -methylpropoxy and l-ethyl-2- methylpropoxy and the different isomers. This definition also applies to alkoxy as a part of a composite substituent, for example haloalkoxy, alkenylalkoxy, alkynylalkoxy, etc., unless specifically defined elsewhere.
"Alkoxyalkyl" denotes alkoxy substitution on alkyl. Examples of "alkoxyalkyl" include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2. This definition also applies to alkoxyaikyi as a part of a composite substituent, for example haloalkoxyalkyl, unless specifically defined elsewhere.
The term "alkoxyalkoxy" denotes alkoxy substitution on alkoxy.
The term "alkylthio" includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, propylthio, 1 -methylethylthio, butylthio, 1-methylpropyithio, 2-methylpropylthio, 1, 1 - dimethyiethylthio, pentylthio, 1 -methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2- dimethylpropylthio, 1-ethylpropylthio, hexyithio, 1 , 1-diniethyl.propylthio, 1 ,2- dimethylpropylthio, 1 -methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4- methylpentylthio, 1 , 1 -dimethylbutylthio, 1 ,2-dimemylbutylthio, 1 ,3-dimethylbutylthio, 2,2- dimethylbutylthio, 2,3 -dimethylbutylthio, 3,3-dimethylbutyithio, 1-ethylbutylthio, 2- ethylbutylthio, 1 , 1 ,2-trirnethylpropylthio, 1 ,2,2-trimethylpropylthio, I -ethyl- 1 -methylpropylthio and l-ethyl-2-methylpropyithio and the different isomers.
Halogenocycloalkyi, halogenocycloalkenyi, alkylcycloalkyl, cycloaikylalkyl, cycioalkoxyalkyl, alkylsuifinylalkyl, alkylsulfonylalkyl, halogenoalkylcarbonyl, cycloalkylcarbonyl, halogenoalkoxylalkyl, and the like, are defined analogously to the above examples.
The term "Aikyithioalkyl" denotes alkylthio substitution on alky] . Representative examples of "alkylthioalkyl" or "alkylsulfanylalkyl" include -CH2SCH2, -CH2SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2 and CH3CH2SCH2CH2. "Alkylthioalkoxy" denotes alkylthio substitution on alkoxy. The term "cycloalkylalkylamino" denotes cycloalkyi substitution on aikyl amino. This definition also applies to alkoxy as a part of a composite substituent, for example haloalkoxy, alkenylaikoxy, alkynylalkoxy, etc., unless specifically defined elsewhere.
The terms alkoxyalkoxyalkyl, alkyiaminoalkyl, dialkylaminoalkyl, cycloalkylaminoalkyl, cycloalkylaminocarbonyi and the like, are defined analogously to "alkylthioalkyl" or cycloalkylalkylamino .
The term "Al koxy carbonyl" is an alkoxy group bonded to a skeleton via a carbonyl group (-CO- ). This definition also applies to alkoxycarbonyi as a part of a composite substituent, for example cycloalkylalkoxycarbonyl and the like, unless specifically defined elsewhere.
The term "Alkoxycarbonylalkylamino" denotes alkoxy carbonyl substitution on alkyi amino. "Alkylcarbonylalkylamino" denotes alkyi carbonyl substitution on alkyi amino. The terms alkylthioaikoxycarbonyl, cycloalkylalkylaminoalkyl and the like are defined analogously.
Examples of "alkylsulfinyl" include but are not limited to methylsulphinyl, ethylsulphinyl, propyisulphinyl, 1 -methylethylsulphinyL butyl sulphinyl, 1-methylpropylsulphinyl, 2- met ylpropylsulphinyl, 1 , 1 -dimethylethylsulphinyl, pentyl sulphinyl, 1 -methylbutylsulphinyl, 2- methylbutylsulphinyl, 3-methylbutylsuiphinyi, 2,2-dimethylpropyisulphinyl, 1- ethylpropylsulphinyl, hexylsuiphinyi, 1, 1-dimethylpropylsulphinyl, 1,2-dimethylpropylsulphinyl, 1-methylpentylsulphinyl, 2-methylpentylsulphinyl, 3-methylpentylsulphinyl, 4- methylpentylsulphinyl, 1 , 1 -dimethylbutylsulphinyl, 1 ,2-dimethylbutylsulphinyl, 1,3- dimethylbutylsulphinyl, 2,2-dimethylbutylsulphinyl, 2,3-dimemylbutylsulphinyl, 3,3- dimethylbutylsulphinyl, 1-ethylbutylsulphinyl, 2-ethylbutylsulphinyl, 1,1,2- trimethylpropylsulphinyl, 1 ,2,2-trimethylpropyl.sulphinyl, 1 -ethyl- 1-methylpropylsulphinyl. and
1 - ethyl -2-methylpropylsulphinyl and the different isomers. The term "arylsulfmyl" includes Ar- S(O), wherein Ar can be any carbocyle or heterocylcie. This definition also applies to alkylsulphinyl as a part of a composite substituent, for example haloaikyisulphiny! etc., unless specifically defined elsewhere.
Examples of "alkylsulfonyl" include but are not limited to methylsulphonyi, ethylsulphonyl, propyl sulphonyl, 1-methylethylsulphonyl, butylsulphonyl, 1 -methylpropylsulphonyl, 2- methylpropylsulphonyl, 1,1 -dimethylethylsulphonyl, pentylsulphonyl, l-methylbutyl sulphonyl,
2- methylbutylsulphonyl, 3-methylbutylsulphonyl, 2,2-dimethylpropylsulphonyl, 1 - eth ylpropyl sul honyl, hexylsulphon yl , 1,1 -dimethyl propylsulphon yl , 1,2- dimethylpropylsulphonyl, 1-methylpentylsulphonyl, 2-methylpentylsulphonyl, 3- methylpentylsulphonyl, 4-methylpentyl sulphonyl, 1 , 1 -dimethylbutylsulphonyl, 1 ,2- dimethyibutylsuiphonyl, 1,3-dimethylbutylsulphonyl, 2,2-dimethylbutylsulphonyl, 2,3- dimethylbuty lsulphon yl, 3,3 -dimethylbutylsulphonyl, 1 -ethylbutyl sulphonyl, 2- ethylbutylsulphonyl, 1 , 1 ,2-trimethylpropylsulphonyl, 1 ,2,2-trimeth ylpropyl sulphonyl, 1 -ethyl- 1 - methylpropylsulphonyl and l-ethyl-2-methylpropylsulphonyl and the different isomers. The term "arylsulfonyl" includes Ar-S(0)2, wherein Ar can be any carbocyle or heterocylcie. This definition also applies to alkylsuiphonyl as a part of a composite substituent, for example alkylsulphonylalkyl etc., unless defined elsewhere.
"Aikyiamino", "dialkylamino", and the like, are defined analogously to the above examples. The term "carbocycle" includes "aromatic carbocyclic ring system" and "nonaromatic carbocylic ring system" or polycyclic or bicyeiic (spiro, fused, bridged, nonfused) ring compounds in which ring may be aromatic or non-aromatic (where aromatic indicates that the Huckel rule is satisfied and non-aromatic indicates that the Huckel rule is not statisfied).
The term "hetero" in connection with rings refers to a ring in which at least one ring atom is not carbon and which can contain 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs.
The term "Heteroaryl" means 5 or 6-membered, fully unsaturated monocyclic ring system containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur; if the ring contains more than one oxygen atom, they are not directly adjacent; 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom as ring members, for example (but not limited thereto) 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazoiyl, 5-isoxazoiyl, 3-isothiazolyi, 4-isofhiazoiyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4- thiazolyi, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, l,2,4-oxadiazol-3-yl, l,2,4-oxadiazol-5-yl, l,2,4-thiadiazol-3-yl, L2,4-thiadiazol-5-yl, l,2,4-triazol-3-yl, l,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol- 2-yl and l,3,4-triazol-2-yl; nitrogen -bonded 5-membered heteroaryl containing one to four nitrogen atoms, or benzofused nitrogen- bonded 5-membered heteroaryl containing one to three nitrogen atoms: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms as ring members and in which two adjacent carbon ring members or one nitrogen and one adjacent carbon ring member may be bridged by a buta-l,3-diene-l,4-diyl group in which one or two carbon atoms may be replaced by nitrogen atoms, where these rings are attached to the skeleton via one of the nitrogen ring members, for example (but not limited to) 1 -pyrrol yl, 1-pyrazolyl, 1 ,2,4-triazol-l- yl, 1- imidazolyl, 1,2,3-triazol-i-yl and 1,3,4-triazol-l-yl.
6-membered heteroaryl which contains one to four nitrogen atoms: 6-membered heteroaryl groups which, in addition to carbon atoms, may contain, respectively, one to three and one to four nitrogen atoms as ring members, for example (but not limited thereto) 2-pyridinyl, 3- pyridinyL 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyL 4-pyrimidinyl, 5-pyrimidinyL 2-pyrazinyl, l,3,5-triazin-2-yl, l,2,4-triazin-3-yl and 1,2,4, 5-tetrazin-3-yl; benzofused 5-membered heteroaryl containing one to three nitrogen atoms or one nitrogen atom and one oxygen or sulphur atom: for example (but not limited to) indol-l-yi, indol-2-yl, indol-3-yl, indol-4-yl, indol- 5-yl, indol-6-yl, indol-7-yl, benzimidazol-l-yl, benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5-yl, indazol-l-yl, indazoi-3-yi, indazoi-4-yl, indazol-5-yi, indazoi-6-yl, indazoi-7- yl, indazol-2-yl, l-benzofuran-2-yl, l-benzofuran-3-yl, l-benzofuran-4-yl, l-benzofuran-5-yl, 1 - benzofuran- 6-yl, l-benzofuran-7-yl, l-benzothiophen-2-yl, l-benzothiophen-3-yl, 1- benzothiophen-4-yl, 1- benzothiophen-5-yl, l-benzothiophen-6-yl, l-benzothiophen-7-yl, 1,3- benzothiazol-2-yl, 1 ,3- benzothiazol-4-yl, l,3-benzothiazol-5-yl, l,3-benzothiazol-6-yl, 1,3- benzothiazol-7-yl, l,3-benzoxazol-2-yl, l,3-benzoxazol-4-yl, l,3-benzoxazol-5-yl, 1 ,3- benzoxazol-6-yl and l,3-benzoxazol-7-yl; benzofused 6-membered heteroaryl which contains one to three nitrogen atoms: for example (but not limited to) quinolin-2-yl, quinolin-3-yl, quinolin-4- yi, quinolin-5-yl, quinolin-6-yl, quinoiin-7-yi, quinolin-8-yl, isoquinolin-l-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yi and isoquinolin-8-yl. This definition also applies to heteroaryl as a part of a composite substituent, for example heteroarylalkyi etc., unless specifically defined elsewhere.
The term "aromatic" indicates that the Huckel rule is satisfied and the term "non-aromatic" indicates that the Huckel rule is not satisfied.
The term lieterocycle means three- to fifteen-membered, preferably three- to tweleve-membered, saturated or unsaturated or partially unsaturated heterocycle containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur: mono, bi- or tricyclic heterocycles which contain, in addition to carbon ring members, one to three nitrogen atoms and/or one oxygen or sulphur atom or one or two oxygen and/or sulphur atoms; if the ring contains more than one oxygen atom, they are not directly adjacent; for example (but not limited to) oxiranyl, aziridinyl,
2- tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl,
3- pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyi, 3-isothiazolidmyi, 4- isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazoiidinyl, 5-pyrazolidinyl, 2- oxazolidmyi, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2- imidazolidinyl, 4-imidazolidinyl, l,2,4-oxadiazolidin-3-yi, l,2,4-oxadiazolidin-5-yl, 1,2,4- thiadiazolidin-3-yl, l ,2,4-thiadiazolidin-5-yl, l,2,4-triazolidin-3-yl, l,3,4-oxadiazolidin-2-yl, l,3,4-thiadiazolidin-2-yl, l,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4- dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4- dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3- pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3- isoxazolin-4-yi, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2- isothiazolin-3-yi, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl,
4- isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3- dihydropyrazol-l-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-l-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol- 4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-i-yi, 4,5-dihydropyrazol-3-yl, 4,5- dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl,
2.3- dihydrooxazol-4-yl, 2,3-dihydrooxazoi-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl,
3.4- dihydrooxazol-4-y}, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, l,3-dioxan-5-yl, 2- tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4- hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5 - hexahydropyrimidinyl, 2-piperazinyl, l,3,5-hexahydrotriazin-2-yl and l,2,4-hexahydrotriazin-3- yl. This definition also applies to heterocyclyl as a part of a composite substituent, for example heterocyclylalkyl etc., unless specifically defined elsewhere. "Trialkylsilyl" includes 3 branched and/or straight-chain alkyl radicals attached to and linked through a silicon atom such as trimethylsilyl, triethylsilyl and t-butyl-dimeihylsilyl. " alotriaikyisilyl" denotes at least one of the three alkyl radicals is partially or fully substituted with halogen atoms which may be the same or different, "Alkoxytrialkylsilyl" denotes at least one of the three alkyl radicals is substituted with one or more alkoxy radicals which may be the same or different, "Trialkylsilyloxy" denotes a trialkylsilyl moiety attached through oxygen.
Examples of "alkylcarbonyl" include C(0)CH3, C(0)CH2CH2Ce3 and C(0)CH(CH3)2. Examples of "alkoxycarbonyi" include CH3OC(=0), CH3CH2OC(=0), CH3CH2CH2OC(=0), (CH3)2CHOC(=0) and the different butoxy -or pentoxycarbonyl isomers. Examples of "alkylaminocarbonyl" include CH3NHC(=0), CH3CH2NHC(=0), CH3CH2CH2 HC(=0), (CH3)2CHNHC(=0) and the different butylamino -or pentylaminocarbonyl isomers. Examples of "dialkylaminocarbonyl " include (CH3)2NC(=0), (Ce3CH2)2NC(=0), CH3CH2(CH3)NC(=0), CH3CH2CH2(CH3)NC(=0) and (CH3)2CHN(CH3)C(=0). Examples of "alkoxyalkylcarbonyl" include CH3OCH2C(=0), CH3OCH2CH2C(=0), CH3CH2OCH2C(=0), CH3CH2CH2CH2OCH2C(=0) and CH3CH2OCH2CH2C(=0). Examples of "alkylthioalkylcarbonyl" include CH3SCH2C(=0), CH3SCH2CH2C(=0), CH3CH2SCH2C(=0), CH3CH2CH2CH2SCH2C(=0) and CH3CH2SCH2CH2C(=0). The terni haloalkylsufonylaminocarbonyl, alkylsulfonylaminocarbonyl, alkylthioaikoxycarbonyl, alkoxycarbonyi alkyl amino and the like are defined analogously
Examples of "aikylaminoaikyiearbonyr include CH3NHCH2C(=0), CH3NHCH2CH2C(=0), CH3CH2NHCH2C(=0), CH3CH2CH2CH2NHCH2C(=0) and CH3CH2NHCH2CH2C(=0).
The term "carbamoyl" or "Amide" means A-R'C(=0)NR"-B, wherein R' and R" indicates substituents and A and B indicate any group.
The term "thioamide" means A-R'C(=S)NR"-B, wherein R' and R" indicates substituents and A and B indicate any group.
The total number of carbon atoms in a substituent group is indicated by the "Cj-Cj" prefix where i and j are numbers from 1 to 21. For example, Ci-C3 alkylsulfonyl designates methyl sulfonyl through propylsulfonyl; C2 alkoxyalkyl designates CH3OCH2; C3 alkoxyalkyl designates, for example, CH3CH(OCH3), CH3OCH2CH2 or CH3CH2OCH2; and C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH3CH2CH2OCH2 and CH3CH2OCH2CH2. In the above recitations, when a compound of Formula I is comprised of one or more heterocyclic rings, all substituents are attached to these rings through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen. When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1, said substituents (when they exceed 1) are independently selected from the group of defined substituents. Further, when the subscript m in (R)m indicates an integer ranging from for example 0 to 4 then the number of substituents may be selected from the integers between 0 and 4 inclusive.
When a group contains a substituent which can be hydrogen, for example R] or R2, then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being un-substituted.
The present invention also relates to a method for controlling unwanted microorganisms, wherein compounds of the formula (I) are applied to the microorganisms and/or in their habitat.
The present invention further provides a method for protecting seeds against unwanted microorganisms by using seed treated with at least one compound of the formula (I).
The compounds of the formula (I) can possess potent microbiocidal activity and can be used for the control of unwanted microorganisms, such as fungi, nematodes and bacteria, in crop protection and in the protection of such materials.
The compounds of the formula (I) can possess very good fungicidal properties and can be used in crop protection, for example for control of Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes .
The compounds of the formula (I) can be used as nematicides in crop protection, for example, for control of Rhabditida, Dorylaimida, and Tryplonchida.
The compounds of the formula (I) can be used as bactericides in crop protection, for example, for control of Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
The compounds of the formula (I) can be used as herbicides and can be effective against a broad spectrum of economically important mono- and dicotyledonous harmful plants. Monocotyledonous broad-leaved weed species may include Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria and Cyperus species from the annual group and perennial species Agropyron, Cynodon, Imperata and Sorghum and also perennial Cyperus species. Dicotyledonous broad-leaved weed species may include Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Sida, Matricaria and Abutilon on the annual side, and also Convolvulus, Cirsium, Rumex and Artemisia in the case of the perennial broad- leaved weeds. Harmful plants that occur in rice, such as, for example, Echinochloa, Sagittaria,
Alisma, Eieocharis, Scirpus and Cypems, can be controlled by the compounds of formula (I). The compounds of the formula (I) can be used for curative or protective control of phytopathogenic fungi. The invention therefore also relates to curative and protective methods for controlling phytopathogenic fungi by the use of the inventive active ingredients or compositions, which are applied to the seed, the plant or plant parts, the fruit or the soil in which the plants grow.
The compounds of the formula (I) can be used for controlling or preventing against phytopathogenic fungi, bacteria, insects, nematodes, mi es of agricultural crops and or horticultural crop s .
The compounds of the formula (I) can be used in crop protection, wherein the agricultural crops are cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbitaceae, oleaginous plants, tobacco, coffee, tea, cacao, sugar beet, sugar cane, cotton, potato, tomato, onions, peppers and other vegetables, and ornamentals.
According to the invention, as defined above a carrier is a natural or synthetic, organic or inorganic substance with which the active ingredients are mixed or combined for better applicability, in particular for application to plants or plant parts or seed. The carrier, which may be solid or liquid, are generally inert and should be suitable for use in agriculture.
Useful solid carriers include for example ammonium salts and natural rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic rock flours, such as finely divided silica, alumina and silicates; useful solid carriers for granules include: for example, crashed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and also synthetic granules of inorganic and organic flours, and granules of organic material such as paper, sawdust, coconut shells, maize cobs and tobacco stalks; useful emulsifiers and/or foam-formers include: for example nonionic and anionic emulsifiers, such as polyoxyethvlene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryi polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates and also protein hydrolysates; suitable dispersants are nonionic and/or ionic substances, for example from the classes of the alcohol-POE and/or -POP etliers, acid and/or POP POE esters, alkylaryi and/or POP POE ethers, fat and/or POP POE adducts,
POE- and/or POP-polyol derivatives, POE- and/or POP-sorbitan or -sugar adducts, alkyl or aryl sulphates, alkyl- or arylsulphonates and alkyl or aryl phosphates or the corresponding PO-ether adducts. Additionally, suitable are oligo- or polymers, for example those derived from vinylic monomers, from acrylic acid, from EO and/or PO alone or in combination with, for example, (poly) alcohols or (poly) amines. It is also possible to use lignin and its sulphonic acid derivatives, unmodified and modified celluloses, aromatic and/or aliphatic sulphonic acids and also their adducts with formaldehyde.
The active ingredients can be applied as such or converted to the customary formulations or in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, emulsions, water- or oil-based suspensions, powders, wettabie powders, pastes, soluble powders, soluble tablets, dusts, soluble granules, granules for broadcasting, suspoemulsion concentrates, natural products impregnated with active ingredient, synthetic substances impregnated with active ingredient, nutrients and also microencapsulations in polymeric substances. Application is accomplished in a customary manner, for example by watering, spraying, atomizing, nursery boxes, broadcasting, dusting, foaming, spreading-on and the like. It is also possible to deploy the active ingredients by the ultra-low volume method or to inject the active ingredient preparation or the active ingredient itself into the soil. It is also possible to treat the seeds of the plants.
The active ingredients can be further converted to the nanoformulation with intent to further improve water solubility, thermal stability, bioavailability, sensory attributes, and physiological performance.
Furthermore, the choice of the type of formulation will depend on the specific use.
The formulations mentioned can be prepared in a manner known per se, for example by mixing the active ingredients with at least one customary extender, solvent or diluent, emulsifier, dispersant and/or binder or fixing agent, wetting agent, a water repellent, if appropriate siccatives and UV stabilizers and if appropriate dyes and pigments, antifoams, preservatives, secondary- thickeners, stickers, gibberellins and also other processing auxiliaries.
The present invention includes not only formulations which are already ready for use and can be deployed with a suitable apparatus to the plant or the seed, but also commercial concentrates which have to be diluted with water prior to use.
The auxiliaries used may be those substances which are suitable for imparting particular properties to the composition itself and/or to preparations derived therefrom (for example spray liquors, seed dressings), such as certain technical properties and/or also particular biological properties. Typical auxiliaries include extenders, solvents and carriers.
Suitable extenders are, for example, water, polar and nonpolar organic chemical liquids, for example from the classes of the aromatic and nonaromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which may optionally also be substituted, etherified and/or esterified), the ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly) ethers, the unsubstituted and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, the sulphones and sulphoxides (such as dimethyl sulphoxide). Liquefied gaseous extenders or carriers are understood to mean liquids which are gaseous at standard temperature and under standard pressure, for example aerosol propellants such as halohydrocarbons, or else butane, propane, nitrogen and carbon dioxide.
In the formulations it is possible to use tackifiers such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids. Further additives may be mineral, vegetable oils and methylated seed oils.
If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Useful liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, or else water.
Compositions comprising compounds of the formula (I) may additionally comprise further components, for example surfactants. Suitable surfactants are emulsifiers and/or foam formers, dispersants or wetting agents having ionic or nonionic properties, or mixtures of these surfactants. Examples thereof are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic esters, taurine derivatives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty esters of polyois, and derivatives of the compounds containing sulphates, sulphonates and phosphates, for example alkylaryl poiyglycoi ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, protein hydrolysaies, lignosulphite waste liquors and methylcellulose. The presence of a surfactant is necessary if one of the active ingredients and/or one of the inert carriers is insoluble in water and when application is effected in water. The proportion of surfactants is between 5 and 40 per cent by weight of the inventive composition.
It is possible to use dyes such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
Further additives may be perfumes, mineral or vegetable, optionally modified oils, waxes and nutrients (including trace nutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. Additional components may be stabilizers, such as cold stabilizers, presen'atives, antioxidants, light stabilizers, or other agents which improve chemical and/or physical stability.
If appropriate, other additional components may also be present, for example protective colloids, binders, adhesives, thickeners, thixotropic substances, penetrants, stabilizers, sequestering agents, complex formers. In general, the active ingredients can be combined with any solid or liquid additive commonly used for formulation purposes.
The formulations contain generally between 0.05 and 99% by weight, 0.01 and 98% by weight, preferably between 0.1 and 95% by weight, more preferably between 0.5 and 90% of active ingredient, most preferably between 10 and 70% by weight. The formulations described above can be used for controlling unwanted microorganisms, in which the compositions comprising compounds of the formula (I) are applied to the microorganisms and/or in their habitat.
The present invention further relates to a composition for controlling unwanted microorganisms comprising at least one of the compounds of the formula (I) and one or more inert carrier. The inert carrier further comprises agriculturally suitable auxiliaries, solvents, diluents, surfactants and/or extenders and the like.
The present invention further relates to a composition for controlling unwanted microorganisms, comprising at least one of the compounds of the formula (I) and/or one or more active compatible compounds selected from fungicides, bactericides, acaricides, insecticides, nemadcides, herbicides, biopesticides, plant growth regulators, antibiotics, nutrients and/or mixtures thereof.
The present invention further relates to a composition wherein the concentration of compounds having general formula (I) ranges from 1 to 90% by weight with respect to the total weight of the composition, preferably from 5 to 50% by weight with respect to the total weight of the composition.
Further the agrochemicai compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, more preferably between 1 and 70%, and in particular between 10 and 60%, by weight of active substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum). For the purposes of treatment of plant propagation materials, particularly seeds, solutions for seed treatment (IS), Suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (OS), water- dispersible powders for slurry treatment (WS), water- soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels (GF) are usually employed. The compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready-touse preparations. Application can be carried out before or during sowing. Methods for applying compound I and compositions thereof, respectively, onto plant propagation material, especially seeds, include dressing, coating, pelleting, dusting, and soaking as well as in-furrow application methods. Preferably, compound I or the compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting. When employed in plant protection, the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2kg per ha, more preferably from 0.05 to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha. In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 40 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required. When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts WO 2017/081312 PCT/EP2016/077524 customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1kg, of active substance per cubic meter of treated material. Compounds of the formula (I) according to this invention, as well as salts, N-oxides, metal complexes, stereoisomers or polymorphs can be used as such or in formulations thereof and can be mixed with known mixing partners in order to broaden, for example, the activity spectrum or to prevent development of resistance. Useful mixing partners include, for example, known fungicides, insecticides, acaiicides, nematicides, biopesticides and bactericides. A mixture with other known active ingredients, such as herbicides, or with nutrients and growth regulators, safeners and/or semiochemicals, is also possible.
Examples for such chemical ingredients are given herein in a not iimitating way. Some of them are specified herein by their common names that are known and described, for example in The Pesticide Manual 17th Ed., or can be searched in the internet (e.g. under www.alanwood.net/pesticides). Others are described by their systematic name following the IUPAC rules for nomenclature.
Ail named mixing partners of the classes (A) to (O) as described below can, if their functional groups enable this, optionally form salts with suitable bases or acids, appear as stereoisomers, even if not specifically mentioned in each case, or as polymorphs. They are also understood as being included herein. These examples are: A) Inhibitors of the ergo sterol biosynthesis, for example (A01) aldimorph, (A02) azaconazole, (A03) bitertanol, (A04) bromuconazole, (AOS) cyproconazole, (A06) diclobutrazole, (A07) difenoconazole, (AOS) diniconazole, (A09) diniconazole-M, (A 10) dodemorph, (Al l) dodemorph acetate, (A12) epoxiconazole, (A13) etaconazole, (A14) fenarimol, (A 15) fenbuconazole, (A16) fenhexamid, (A17) fenpropidin, (A18) fenpropimorph, (A19) fluquinconazole, (A20) flurprimidol, (A21) flusilazole, (A22) flutriafol, (A23) furconazole, (A24) furconazole-cis, (A25) hexaconazole, (A26) imazalil, (A27) imazalil sulfate, (A28) imibenconazole, (A29) ipconazole, (A30) metconazole, (A31) myclobutanil, (A32) naftifine, (A33) nuarimol, (A34) oxpoconazole, (A35) paclobutrazol, (A36) pefiirazoate, (A37) penconazole, (A38) piperalin, (A39) prochloraz, (A40) propiconazole, (A41) prothioconazole, (A42) pyributicarb, (A43) pyrifenox, (A44) quinconazole, (A45) simeconazole, (A46) spiroxamine, (A47) tebuconazole, (A48) terbinafine, (A49) tetraconazole, (A50) triadimeton, (A51) triadimenol, (A52) tridemorph, (A53) triflumizole, (A54) triforine, (A55) triticonazole, (A56) uniconazole, (A57) uniconazole-p, (A58) viniconazole, (A59) voriconazole, (A60) l-(4- chlorophenyl)-2-(lH-l,2,4-triazol-l-yl)cycloheptanol, (A61) methyl l-(2,2-dimethyl-2,3- dihydro- 1 H-inden- 1 -yl)- 1 H-imidazole-5-carboxylate, ( A62) N'- { 5-(difluoromethyl)-2-methyl-4- [3-(trimethyisiiyl) propoxy]phenyl}-N-ethyl-N-methylinndoformarriide, (A63) N-ethyl-N- methyl-N'-{ 2-methyl-5-( fluoromethyl)-4-[3-(trimemylsilyl)propoxy]phenyl} imidoformamide, (A64) 0-[ l-(4-methoxyphenoxy)-3,3-dimemylbutan-2-yl]-lH-imidazole-l-carbothioate, (A65) Pyrisoxazole, (A66) 2-{ [3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4- dihydro-3H-l,2,4-triazole-3-thione, (A67) l-{ [3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran- 2-yl]methyl}-lH-l,2,4-triazol-5-yl thiocyanate, (A68) 5-(allylsulfanyl)-l-{ [3-(2-chlorophenyl)- 2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-lH-l,2,4-triazole, (A69) 2-[l-(2,4-dichlorophenyl)-5- hydroxy-2,6,6-trimethymeptan-4-yl]-2,4-dmydro-3H-l,2,4-triazole-3-thione, (A70) 2- { [rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl) oxiran-2-yl]methyl } -2,4-dihydro-3H- l,2,4-(riazole-3-thione, (A71) 2-{ [rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran- 2-ylJmethyl}-2,4-dihydro-3H-l,2,4-triazole-3-thione, (A72) 1 -{ [rel(2R,3S)-3-(2-chlorophenyl)- 2-(2,4-difluorophenyl)oxiran-2-yl]methyl} - 1 H- l,2,4-triazol-5-yl thiocyanate, (A73) 1 - { [rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-di†luoropheny})oxiran-2-yilniethy
yi thiocyanate, (A74) 5-(allylsuIfanyl)-l-{ [rel(2R,3S)-3-(2-chlorophenyI)-2-(2,4- difluorophenyl)oxiran-2-yl]methyl } - 1H- 1 ,2,4-triazole, (A75) 5-(allylsulfanyl)- 1 - { [rel(2R,3R)-3- (2-chlorophenyl)-2-(2,4-difluorophenyI) oxiran-2- -yl] methyl } - 1H- 1 ,2,4-triazole, (A76) 2- [(2S,4S,5S)-l-(2,4~ dichlorophenyl) -5-hydroxy-2,6,6-trime lheptan-4-yl]-2,4-dihydro-3H- l,2,4-triazole-3-thione, (A77) 2-[(2R,4S,5 S)-l -(2,4-dichlorophenyl)-5-hydroxy-2,6,6- trimethylheptan-4~yl]~2,4-dihydro-3H ,2,4 riazole-3-thione, (A78) 2-[(2R,4R,5R)-l-(2,4- dichlorophenyl)-5-hydroxy-2,6,6-trimetiiym
(A79) 2-[(2S,4R,5R)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethymeptan-4-yl]-2,4-di ydro- 3H-l ,2,4-triazole-3-thione, (A80) 2-[(2S,4S,5R)-l -(2,4-dichlorophenyl)-5-hydroxy-2,6,6- triniethylhepian-4-yl] -2,4-dihydro-3H- 1 ,2,4-triazole-3-thione, (A81 ) 2- [(2R,4S ,5R)- 1 -(2,4- dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-tri
(A82) 2-[(2R,4R,5S)- l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethymeptan-4-yl]-2,4-di ydro- 3H-l ,2,4-triazole-3-thione, (A83) 2-[(2S,4R,5S)-l -(2,4-dichlorophenyl)-5-hydroxy-2,6,6- trimethylheptan-4-yl]-2,4-dihydro-3H- l,2,4-triazole-3-thione, (A84) 2-[4-(4-chlorophenoxy)-2- (trifluoromethyl)phenyl]- 1-(1H- 1,2,4-triazol- 1 -yl)propan-2-ol, (A85) 2-[4-(4-chlorophenoxy)-2- (trifluoromethyl)phenyl]- 1-(1H- 1,2,4-triazol- l-yl)butan-2-ol, (A86) 2-[4-(4-chlorophenoxy)-2- (trif uoromethyl)phenyl]-l-(lH-l,2,4-triazol-l-yl)pentan-2-ol, (A87) 2-[2-chloro-4-(4- chlorophenoxy)phenyl]-l -(lH-1 ,2,4-triazol-l-yl)butan-2-ol, (A88) 2-[2-chloro-4-(2,4- dichlorophenoxy)phenyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)propan-2-ol, ( A89) (2R)-2-( 1 - chlorocyclopropyl)-4- (l.R)-2,2-dichlorocyclopropyl]-l-(lH- 1,2,4-triazol- 1 -yl)butan-2-ol, (A90) (2R)-2-( 1 -chlorocyclopropyl)-4- [( 1 S)-2,2-dichlorocyclopropyl] - 1 -( 1H- 1 ,2,4-triazol- 1 -yl)butan- 2-ol, (A91) (2S)-2-(l.-chlorocyclOpropyl)-4-[(l S)-2,2-dichlorocyclopropyl]-l-(lH-l,2,4-triazol- l-yl)butan-2-ol, (A92) (2S)-2-(l-chlorocyclopropyl)-4-[(lR)-2,2-dichioiOcyclopropyl]-l-(lH- l,2,4-triazol-l-yl)butan-2-ol, (A93) (lS,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl- 1 - ( 1H- 1 ,2,4-triazol- 1 - ylmethyl)cyclopentanol, (A94) ( 1R,2S ,5S)-5-(4-chlorobenzyl)-2- (chloromethyl)-2-niethyl-l -(IH-l ,2,4-triazol- l-ylmethyl)cyclopentanol, (A95) 5-(4- chlorobenzyl)-2- (chloromethyl)-2-methyl- 1 -( 1 H- 1 ,2,4-triazol- 1 -ylmethyl)cyclopentanol
B) Inhibitors of the respiratory chain at complex I or II, for example (B01) bixafen, (B02) boscalid, (B03) carboxin, (B04) cypropamide, (BOS) diflumetorim, (B06) fenfuram, (B07) fluopyram, (B08) flutolanil, (B09) fluxapvroxad, (B IO) furametpyr, (B l l) turmecyclox, (B 12) isopyrazam (mixture of syn-epimeric racemate 1RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR), (B13) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), (B 14) isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (B15) isopyrazam (anti-epimeric enantiomer 1S,4R,9R), (B16) isopyrazam (syn-epimeric racemate 1RS,4SR,9RS), (B17) isopyrazam (syn-epimeric enantiomer 1R,4S,9R), (B18) isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (B 19) mepronil, (B20) oxycarboxin, (B21) penflufen, (B22) penthiopyrad, (B23) pydiflumetofen, (B24) sedaxane, (B25) thifluzamide, (B26) l-methyl-N-[2-(l,l,2,2-tetrailuoroetlioxy)phenyl]-3- (trifluoromethyl)- l.H-pyrazole-4-carbox amide, (B27) 3 -(difluoromethyl)- 1 -methyl-N- [ 2-( 1 , 1 ,2,2- tetrafluoroethoxy)phenyl]-lH-pyrazole-4-cai"boxamide, (B28) 3-(difluoromethyl)-N-[4-fluoro-2- (1,1 , 2,3,3, 3-hexafluoropropoxy)phenyl]-l-methyl-lH-pyrazole-4-carboxamide, (B29) N-[l-(2,4- dichloiOphenyl)-l-metlioxypropan-2-yl]-3-(difluoromethyl)-l-methyl-lH-pyrazole-4- carboxamide, (B30) 5,8-difluoro-N-[2-(2-fluoro-4-{ [4-(trifluoromethyl)pyridin-2- yl]oxy}pyhenyl)ethyl]quinazolin-4-amine, (B31) benzovindiflupyr, (B32) N-[(l S,4R)-9- (dichloromethylene)- 1 ,2,3 ,4-tetrahydro- 1 ,4-methanonaphthalen-5-yl] -3-(difluoromethyl)- 1 - methyl-l.H-pyrazole-4-carboxaniide, (B33) N- (l.R,4S)-9-(dichloromethylene)-l ,2,3,4- tetrahydro-l,4-methanonaphthalen-5-yl]-3-(difluorometliyl)-l-methyl- lH-pyrazole-4- carboxamide, (B34) 3-(difl.uoromethyl)- l-methyl-N-(l , 1 ,3-trimethyl-2,3-dihydro- 1 H-inden-4- yl)- lH-pyrazole-4-carboxamide, (B35) l ,3,5-trimetliyl-N-(l,l,3-trimethyl-2,3-dihydro-lH- inden-4-yl)- 1 H-pyrazole-4-carboxamide, (B36) 1 -methyl-3-(lrifluoromethyl)-N-( 1 , 1 ,3-trimethyl- 2,3-dihydro- lH-inden-4-yl)- lH-pyrazole-4-carboxamide, (B37) l-methyl-3-(trifluoromethyl)-N- [(3R)-l ,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-lH-pyrazole-4-carboxamide, (B38) 1-methyl-
3- (trifluoromethyl)-N- [(3S)-l,l,3-triniethyl-2,3-dihydro-lH-inden-4-yl]-l.H-pyrazole-4- carboxamide, (B39) 3-(difluoromethyl)-l-mediyl-N-[(3S)-l,l,3-trimethyl-2,3-di ydro-lH-mden-
4- y] j- 1 H-pyrazole-4-carboxamide, (B40) 3-(difluoromethyl)- 1 -methyl-N-[(3R)- 1 , 1,3-tri.methyl- 2,3-di ydro-lH-inden-4-yl]-lH-pyrazole-4-carboxamide, (B41) l,3,5-trimethyl-N-[(3R)- 1,1,3- trimethyl-2,3-dihydro-l H-inden-4-yl]-lH-pyrazole-4-carboxamide, (B42) 1,3,5-trimethyl-N- [(3S)- 1,1,3- trimethyl-2,3-dihydro- lH-inden-4-yl] - lH-pyrazole-4-carboxamide, (B43) benodanil, (B44) 2-chloro-N-( 1 , 1 ,3-trimethyl-2,3-dihydro- lH-inden-4-yl)pyridine-3- carboxamide, (B45) Isofetamid, (B46) l -methyl-3-(trifluoromethyl)-N-[2'- (trif uoromethyl)biphenyl-2-yl] - 1 H-pyrazole-4-carboxamide, (B47) N-(4'-chlorobiphenyl-2-yl)- 3 -( difluoroniethyl) - 1 -methyl- 1 H-pyrazole-4 -carboxamide, (B48) N-(2',4'-dichloiObiphenyl-2-yl)- 3-(difluoromethyl)-l-methyl-lH-pyrazole-4-carboxarnide, (B49) 3-(difluoromethyl)-l-methyl- N-[4'-(trifluoromethyl)biphenyl-2-yl]-lH-pyrazole-4-cai"boxarnide, (B50) N-(2',5 '- difluorobiphenyl-2-yl)-l-methyl-3-(trifluoromethyl)-lH-pyrazole-4-carboxarrn (B51) 3- (difluoroniethy])-] -metl yl-N-[4'-(prop-l-yi -l-y])biphenyl-2-ylj-
(B52) 5-fluoro-l,3-dimethyl-N-[4'-(prop-l-yn-l-yl)biphenyl-2-yl]-lH-pyrazole-4-carboxamide, (B53) 2-chloro-N-[4'-(prop- 1-yi - 1 -yl)bi.phenyl-2-yl]nicotinamide, (B54) 3-(difluoromethyl)-N- [4'-(3,3-dimetliylbut-l-yn-l-yl)biphenyl-2-yl] -l -methyl- lH-pyrazole-4-carboxamide, (B55) N- [4'-(3,3-dimethylbut-l -yn-l-yl)biphenyl-2- yl]-5-fluoro-l ,3-dimethyl-lH-pyrazole-4- carboxamide, (B56) 3-(difluoromethyl)-N-(4'-ethynylbiphenyl-2-yl)-l-methyl-lH-pyrazole-4- carboxamide, (B57) N-(4' -et ynylbiphenyl-2-yl)-5-fluoro- 1 ,3-dimethyl- 1 H-pyrazole-4- carboxamide, (B58) 2-chloro-N-(4'-ethynylbiphenyl-2-yl)nicotinamide, (B59) 2-chloro-N-[4'- (3,3-dimethylbut-l-yn-l-yl)biphenyl-2-yl]nicotinamide, (B60) 4-(difluoromethyl)-2-methyl-N- [4'-(trifluoroniethyl)biphenyl-2-yl]-l.,3-thiazole-5-carboxaniide, (B61 ) 5-fluoro-N-[4'-(3- hydroxy-3-methylbut- 1 -yn- 1 -yl)biphenyl-2-yl] - 1 ,3 -dimethyl- lH-pyrazole-4-carboxamide, (B62) 2-chloro-N- [4 '-(3 -hydroxy- 3 -methylbut- 1 -yn- 1 -yl)biphenyl-2-yl]nicotinamide, (B63 ) 3- (difluoromethyl)-N-[4'-(3-methoxy-3-methylbut-l-yn-l-yl)biphenyl-2-yl]-l-methyl-lH- pyrazole-4-carboxamide, (B64) 5-fluoro-N-[4,-(3-methoxy-3-niethyl.but-l -yn-l-yl)biphenyl-2- yl]-l,3-dimethyl-lH-pyraz.ole-4-carboxarnide, (B65) 2-chloro-N-[4'-(3-methoxy-3-methylbut-l- yn- 1 -yl)biphenyl-2-yl]nicotinamide, (B66) 1 ,3-dimethyl-N-( 1 , 1 ,3-trimethyl-2,3-dihydro- 1H- inden-4-yl)- 1 H-pyrazole-4-carboxamide, (B67) 1 ,3 -dimethyl-N- [(3R - 1 , 1 ,3-trimethyl-2,3- dihydro-l H-inden-4-yl]-l H-pyrazole-4-carboxamide, (B68) l,3-dimethyl-N-[(3S)-l,l ,3- methyl-2,3-dihydro-lH-inden-4-yl]-lH-pyrazole-4-carboxamide, (B69) 3-(difluoromethyl)-N- methoxy-l-me(hyl-N-[l-(2,4,6-trichlorophenyl)propan-2-yl]-lH-pyrazole-4-carboxamide, (B70) 3-(difluoromethyl)-N- (7-fluoro- 1 ,1,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl)- 1 -methyl- 1H- pyrazole-4-carboxamide, (B71) 3-(difluoromethyl)-N-[(3,R)-7-fluoro-l,l,3-trimethyl-2,3- dihydro- 1 H-inden-4-yl ]- 1 -methyl- lH-pyrazole-4-carboxamide, ( B72) 3-(difluoromethy 1 )-N- [(3S)-7-fluoro-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-l-methyl-lH-pyrazole-4- carboxamide.
C) Inhibitors of the respiratory chain at complex III, for e ample (CO! )
ametoctradin, (C02) amisulbrom, (C03) azoxystrobin, (C04) cyazofamid, (COS) coumethoxystrobin, (C06) coumoxystrobin, (C07) dimoxystrobin, (COS) enoxastrobin, (C09) famoxadone, (CIO) fenamidone, (CI 1) fenaminstrobin, (C12) flufenoxystrobin, (CI 3) fluoxastrobin, (C14) kresoxim -methyl, (CIS) metominostrobin, (CI 6) mandestrobin, (C17) orysastrobin, (CI 8) picoxystrobin, (CI 9) pyraclostrobin, (C20) pyrametostrobin, (C21) pyraoxystrobin, (C22) pyribencarb, (C23) triclopyricarb, (C24) trifloxystrobin, (C25) (2E)-2-(2- { [6-(3-chloro-2-methylphenoxy)-5-f uoropyi"imidin-4-yl]oxy}phenyl)-2-(methoxyiim
methylacetamide, (C26) (2E)-2-(methoxyimino)-N-methyl-2-(2-{ [({(1Ε)-1-[3- (tritluoromethyl)pher!yljethylidene] amino)oxy]methyl} phenyl) acetamide, (C27) (2E)-2- (methoxyimino)-N-methyl-2- { 2 - [(E)-( { 1 - [3 -
(trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}acetamide, (C28) (2E)-2-{2-[({ [(! E)-l - (3-{ [(E)- l-fluoro-2-phenylvinyl]oxy} phenyl)ethylidene] amino}oxy)methyl]phenyl}-2- (methoxyimino)-N-methylacetamide, (C29) Fenaminostrobin, (C30) 5-methoxy-2-methyl-4-(2- { [({ ( IE)- l-[3-(trifluorometliyl)phenyl]ethylidene } arnino)oxy]methyl}phenyl)-2,4-dihydro-3H-
1.2.4- triazol-3-one, (C31) methyl (2E)-2-{2-[({cyclopropyl[(4- methoxyphenyl)imino]methyl}sulfanyl)methyl]phenyl} -3-methoxyacrylate, (C32) N-(3-ethyl-
3.5.5- methylcyclohexyl)-3-formamido-2-hydroxybenzamide, (C33) 2-{2-[(2,5- dimethylphenoxy )methyl]phenyl ) -2-methoxy-N-methylacetamide, (C34) 2-{2-[(2,5- dimethylphenoxy)methyl]phenyl} -2-methoxy-N-methylacetamide, (C35) (2E,3Z)-5-{ [l-(4- :hIorophenyl)-lH-pyrazoI-3-yI]oxy}-2-(methoxyi^
D) Inhibitors of the mitosis and cell division, for example (DOT) benomyl, (D02) carbendazim, (D03) chlorfenazole, (D04) diethofencarb, (D05) ethaboxam, (D06) fluopicolide, (D07) fiiberidazole, (DOS) pencycuron, (D09) thiabendazole, (D1.0) thiophanate-methyl, (Dl l) thiophanate, (D12) zoxamide, (D13) 5-chloro-7-(4-methylpiperidin- l-yl)-6-(2,4,6- trifluorophenyl)[l,2,4]triazol.o l ,5-aJpyrimidine, (D14) 3-chloro-5-(6-chloropyridin-3-yl)-6- methyl-4-(2,4,6- trifluorophenyl) pyridazine. E) Compounds capable to have a multisite action, for example (E01) bordeaux
mixture, (E02) captafol, (E03) captan, (E04) chlorothalonil, (EOS) copper hydroxide, (E06) copper naphthenate, (E07) copper oxide, (EOS) copper oxychloride, (E09) copper(2+) sulfate, (E10) dichlofluanid, (El l) dithianon, (E12) dodine, (E13) dodine free base, (E14) ferbam, (El 5) fluorofoipet, (El 6) folpet, (El 7) guazatine, (E18) guazatine acetate, (El 9) iminoctadine, (E20) iminoctadine albesilate, (E21) iminoctadine triacetate, (E22) mancopper, (E23) mancozeb, (E24) maneb, (E25) metiram, (E26) metiram zinc, (E27) oxine- copper, (E28) propamidine, (E29) propineb, (E30) sulfur and sulfur preparations including calcium poiysulfide, (E31) thiram, (E32) tolylfluanid, (E33) zineb, (E34) ziram, (E35) anilazine. F) Compounds capable to induce a host defence, for example (F01) acibenzolar-S-methyl, (F02) isotianil, (F03) probenazole, (F04) tiadinil, (F05) laminarin.
G) Inhibitors of the amino acid and/or protein biosynthesis, for example (G01) andoprim, (G02) blasticidin-S, (G03) cyprodinil, (G04) kasugamycin, (G05) kasugamycin hydrochloride hydrate, (G06) mepanipyrim, (G07) pyrimethanil, (G08) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4- dihydroisoquinolin-l-yl)quinoline, (G09)oxytetracycline,(G10)streptomycin.
H) Inhibitors of the ATP production, for example (HOI) fentin acetate, (H02) fentin chloride, (H03) fentinhydroxide, (H04) silthiofam.
I) Inhibitors of the cell wall synthesis, for example (101) benthiavalicarb, (102) dimethomorph, (103) flumorph, (104) iprovalicarb, (105) mandipropamid, (106) polyoxins, (107) polyoxorim, (108) vaiidamycin A, (109) valifenaiate, (110) polyoxin B, (11 1) (2E)-3-(4-tert- butylphenyl)-3-(2-chIoropyri.din-4-yl)-l -(morpholin-4-yI)prop-2-en-l-one, (112) (2Z)-3-(4-tert- butylphenyl)-3-(2-chloropyridii -4-yl)-l-(morpholin-4-yl)prop-2-en-l-one. J) Inhibitors of the lipid and membrane synthesis, for example (J01) biphenyl, (J02) chloroneb, (J03) dicloran, (.104) edifenphos, (J05) etridiazole, (J06) iodocarb, (.107) iprobenfos, (J08) isoprothiolane, (J09) propamocarb, (J 10) propamocarb hydrochloride, (Jl l) prothiocarb, (J12) pyrazophos, (J13) quintozene, (.114) tecnazene, (J 15) toclofos-methyl.
K) Inhibitors of the melanin biosynthesis, for example (K01 ) carpropamid, (K02) diclocymet, (K03) fenoxanil, (K04) phthalide, (K05) pyroquilon, (K06) tolprocarb, (K07)tricyclazole.
L) Inhibitors of the nucleic acid synthesis, for example (L01) benalaxyl, (L02) benalaxyl-M (kiralaxyl), (L03) bupirimate, (L04) clozylacon, (LOS) dimethirimol, (L06) ethirimol, (L07) furalaxyl, (L08) hymexazol, (L09) metalaxyl, (L10) metalaxyl-M (mefenoxam), (Ll l) ofurace, (L12) oxadixyl, (L13) oxoiinic acid, (L1.4)octhilinone.
M) Inhibitors of the signal transduction, for example (M01 ) chlozolinate, (M02) fenpiclonil, (M03) fludioxonil, (M04) iprodione, (M05) procymidone, (M06) quinoxyfen, (M07) vinclozolin, (M08) proquinazid. N) Compounds capable to act as an uncoupler, for example (NOl) binapacryl, (N02) dinocap, (N03) ferimzone, (N04) fluazinam, (N05) meptyldinocap.
O) Further compounds, for example (O01) benthiazole, (O02) bethoxazin, (O03) capsimycin, (O04) carvone, (O05) chinomethionat, (O06) pyriofenone (chlazafenone), (O07) cufraneb, (O08) cyflutenaniid, (O09) cymoxanil, (OlO) cyprosulfamide, (Oi l) dazomet, (012) debacarb, (013) dichlorophen, (014) dichlobentiazox, (015) diclomezine, (016) difenzoquat, (017) difenzoquat metilsulfate, (018) diphenylamine, (019) ecomate, (O20) fenpyrazamine, (021) fenhexamine, (022) flumetover, (023) fluoroimide, (024) flusulfamide, (025) flutianil, (026) fosetyl-aluminium, (027) fosetyl-calcium, (028) fosetyl-sodium, (029) hexachlorobenzene, (O30) irumamycin, (031) isothianil, (032) methasulfocarb, (033) methyl isothiocyanate, (034) metrafenone, (035) mildiomycin, (036) natamycin, (037) nickel dimethyldithiocarbamate, (038) nitrothal-isopropyl, (039) oxamocarb, (040) oxyfenthiin, (041 ) pentachlorophenol and salts, (042) phenothrin, (043) picarbutrazox (044) phosphorous acid and its salts, (045) propamocarb-fosetylate, (046) propanosine-sodium, (047) pyrimorph, (048) pyraziflumid (049) pyrrolnitrine, (050) tebufloquin, (051) tecloflalam, (052) tolnifanide, (053) triazoxide, (054) trichlamide, (055) zarilamid, (056) (3S,6S,7R,8R)-8-benzyl-3-[({3- [(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carb
dioxonan-7-yl 2-methylpropanoate, (057) 1 -(4- { 4-[(5 R)-5-(2,6-difluorophenyl)-4,5-dihydro- 1 ,2- oxazol-3-yl]-l,3-thiazol-2-yl}piperidin-l-yl)-2-[5-methyl-3-(trifluoromethyl)-lH-pyrazol-l^ yljethanone, (058) l.-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-l,2-oxazol-3-yl]-l,3- thiazol-2-yl}piperidin-l-yl)-2-[5-methyl-3-(trifluoromethyl)-lH-pyrazol-l-yl]etlianone (059) oxathiapiprolin, (060) l -(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl-1.H-iniidazole-l- carboxylate, (061) 2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine, (062) 2,3-dibutyl-6- chlorothieno[2,3-d]pyrimidin-4(3H)-one, (063) 2,6-dimethyl-lH,5H-[ l,4]dithiino[2,3-c:5,6- c']dipyrrole- 1 ,3,5,7(2H,6H)-tetrone, (064) 2-[5-methyl-3-(trifluoromethyl)-lH-pyrazol- 1 -yl]- 1- (4-{4-[(5R)-5-phenyl-4,5-dihydro-l,2-oxazol-3-yl]-l,3-t iazol-2-yl}piperidin-l-yl)ethanone, (065) 2-[5-methyl-3-( fl.uoromethyl)-l H-pyrazol-l-yl]-l-(4- {4-[(5S)-5-phenyl-4,5-dihydro- l,2-oxaz.ol-3-yl]-l,3-thiazol-2-yl}piperidin-l-yl)ethanone, (066) 2-[5-methyl-3-
(trifluoromethyl)-l.H-pyrazol-]-ylJ-l -{4-[4-(5-phenyl-4,5-dihydro-l,2-oxaz.ol-3-yl)-l,3- thiazol- 2-yl]piperidin-l-yl}ethanone, (067) 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, (068) 2- chloro-5-[2-chloro-l -(2,6-di†1uo^
(069) 2-phenylphenol and salts, (070) 3-(4,4,5- trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-
1- yl)quinoline, (071) 3,4,5-trichloropyridine-2,6-dicarbonit"rile, (072) 3-chloro-5-(4- chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (073) 4-(4-chlorophenyl)-5-(2,6- difluorophenyl)-3,6-dimet ylpyridazine, (074) 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5- phenylpyridazine, (075) 5-amino-l,3,4-thiadiazole-2-thiol, (076) 5-chloro-N' -phenyl -N'-(prop-
2- yn-l-yl)thiophene-2-sulfonohydrazide, (077) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4- amine, (078) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (079) 5-methyl-6- octyl[ 1 ,2,4] triaz.olo[ 1 ,5-a]pyriniidin-7-amine, (080) ethyl (2Z)-3-amino-2-cyano-3- phenylacrylate, (081 ) N'-(4-{ [3-(4-chlorobenzyl)-l ,2,4-thiadiazol-5-yl]oxy}-2,5- dimethylphenyl)-N-ethyl-N-melhylinTidoforaiamide, (082) N-(4-chlorobenzyl)-3-[3-methoxy-4- (prop-2-yn-l -yloxy)phenyl]propananiide, (083) N-[(4-chl.orophenyl)(cyano)methyl]-3-[3- methoxy-4-(prop-2-yn-l-yloxy)phenyl]propanamide, (084) N-[(5-bromo-3-chloropyridin-2- yl)methyl]-2,4-dichloronicotinamide, (085) N- l -(5-bromo-3-chloropyridin-2-yl)ethyl.]-2,4- dichloronicotinamide, (086) N-[l-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4- iodonicotinamide, (087) N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3- difluorophenyl] methyl } -2-phenylacetamide, (088) N- { (∑' }- -[(cyclopropylmethoxy)imino] [6- (difluoromethoxy)-2,3-difluorophenyl] methyl} -2-phenylacetamide, (089) N'-{4-[(3-tert-butyl- 4-cyano- 1 ,2-thiazol-5-yl)oxy] -2-chloro-5-methylphenyl} -N-ethyl-N-methylimidoformamide, (090) N-methyl-2-(l-{ [5-methyl-3-( fluoromethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-N- ( 1 ,2,3 ,4-tetrahydronaphthalen- 1 -yl)- 1 ,3 -thiazole-4-carboxamide, (091 ) N-methyl-2-( 1 - { [5 - methyl-3-(trifluoromethyl)- lH-pyrazol- 1 -yl] acetyl }piperidin-4-yl)-N- [( 1R)- 1 ,2,3 ,4- tetrahydronaphthalen- 1-yl]- 1 ,3-thiazole-4-earboxamide, (092) N-methyl-2-( 1- { [5-methyl-3- (trifluoromethyl)- lH-pyrazol- 1 -yl] acetyl }piperidin-4-yl)-N- [(1S)-1 ,2,3 ,4- tetrahydronaphthalen- l-y]]-] ,3-thiazole-4-carboxamide, (093) pentyl {6-[( { [(l -methyl-lH-tetrazol-5- yl)(phenyl)methylene] amino } oxy)methyl]pyridin-2-yl } carbamate, (094) phenazine- 1- carboxylic acid, (095) quinolin-8-ol, (096) quinolin-8-ol sulfate (2: 1), (097) tert-butyl {6- [({ [( 1 -methyl- lH-tetrazol-5-yl)(phenyl) methylene] amino }oxy)methyl]pyridin-2-yl} carbamate, (098) (5-bromo-2-methoxy-4-memylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl) methanone, (099) N-[2-(4-{ [3-(4-chlorophenyl)prop-2-yn-l-yl]oxy}-3-methoxyphenyl)thyl]- N2-(methylsulfonyl)valinamide, (0100) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (OlOl) but-3-yn- 1 -yl { 6-[({ [(Z)-(l-methyl- 1 H-tetrazol-5- yl)(phenyl)methylene] amino }oxy)methyl]pyridin-2-yl } carbamate, (0102) 4-amino-5- fluoropyrimidin-2-ol. (tautomeric form: 4-amino-5-fluoropyri.midin-2(lH)-one), (O103) propyl 3,4,5-trihydroxybenzoate, (O104) [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-l,2- oxazol-4-yl](pyridin-3-yl)methanol, (0105) (S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4- difluorophenyl)-l,2-oxazol-4-yl](pyridin-3-yl)methanol, (O106) (R)-[3-(4-chloro-2- fluorophenyl)-5-(2,4-diiluorophenyl)-l,2-oxazol-4-yl](pyridin-3-yl)methanol, (O107) 2-fluoro- 6-(trifluoromemyl)-N-(l,l,3-tiimethyl-2,3-dihydro-lH-inden-4-yl)benzai'nide, (O108) 2-(6- benzylpyridin-2-yl)quinazoline, (O109) 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2- yi]quinazoline, (0110) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-l-yl)quinoline, (0111) Abscisic acid, (0112) N'-[5-bromo-6-(2,3-dihydro-lH-inden-2-yloxy)-2-methylpyridin- 3-yl]-N-ethyl-N-methylimidoformamide, (01 13) N'- {5-bromo-6-[l-(3,5-difluorophenyl)ethoxy] - 2-methylpyridin-3-yi}- -eiliyl-N-meiliyiimidofoniiamide, (0114) N'-{5-bromo-6-[(lR)-l-(3,5- difluorophenyl)ethoxy]-2-methylpyndin-3-yl }-N-ethyl-N-methylimidoformamide, (01 15) N'- {5-bromo-6-[(lS)-l-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N- methylimidoformamide, (01 16) N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy] -2- methylpyiidin-3-yl}-N-ethyl-N-methylimidoformamide, (0117) N'- {5-bromo-6-[(trans-4- isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl ] -N-ethyl-N-methylimidoformamide, (01 18) N- cyclopropyl-3-(dMuoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-l-metih.yl-lH-pyrazole-4- carboxamide, (0119) N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-l- methyl- lH-pyrazole-4-carboxamide, ( 0120) N-(2-tert-butylbenzyl)-N-cyclopropyl-3- (difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (0121) N-(5-chloro-2- ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l-methyl- l.H-pyrazole-4-carboxamide, (0122) N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro- 1 -methyl- 1 H-pyrazole-4-carboxamide, (0123) N-cyclopropyl-3-(difluorometih.yl)-N-(2-ethyl-5- fluorobenzyl)-5-fluoro- 1 -methyl- lH-pyrazole-4-carboxamide, (0124) N-cyclopropyl-3- (difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-l-methyl-l H-pyrazole-4- carboxamide, (0125) N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5- fluoro-1. -methyl- l H-pyrazole-4-carboxamide, (0126) N-(2-cyclopentyl-5-fluorobenzyl)-N- cyclopropy-3-(difluoromethyl)-5-fluoro-l-methyl- lH-pyrazole-4-carboxamide, (0127) N- cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-l-methyl- l.H-pyrazole- 4-carboxamide, (0128) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro- 1 -methyl- lH-pyrazole-4-carboxamide, (0129) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2- isopropyl-5-methylbenzyl)- 1 -methyl- lH-pyrazole-4-carboxamide, (0130) N-cycIopropyl-N-(2- cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4- carboxamide, (0131) N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5- fluoro- 1 -methyl- lH-pyrazole-4-carboxamide, (0132) N-[5-chloro-2-(trifluoromethyl)benzyl] -N- cyclopropyl-3-(difluoromethyl)-5-fluoro-l-memyl-l H-pyrazole-4-carboxamide, (0133) N- cyclopropyl-3-(difluoromethyl)-5-fluoro-l-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-lH- pyrazole-4-carboxamide, (0134) N-[2-chloro-6-(trifluoromethyl)benzyl.]-N-cyclopropyl-3- (difluoromeihyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (0135) N-[3-chloro-2-fluoro- 6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4- carboxamide, (0136) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimetliylbenzyl)-5- fluoro-l-methyl-lH-pyrazole-4-carboxamide, (0137) N-cyclopropyl-3-(difluoromethyl)-5- fluoro-N-(2-isopropylbenzyl)-l -methyl- lH-pyrazole-4-carbothioamide, (0138) N'-(2,5- dimethyl-4-phenoxyphenyl)-N-ethyl-N-med yUmidoformamide, (0139) N'-{4-[(4,5-dichloro- 1 ,3-thiazol-2-yl)oxy] -2,5-dimethylphenyl } -N-ethyl-N-methylimidoformamide, (O140) N-(4- chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)- 1 ,3-dimelhyl- lH-pyrazol-5-amine, (0141) 9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro- 1 ,4-benzoxazepine, (0142) 2- { 2- fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol, (0143) 2-{2-[(7,8-difluoro- 2-methylquinolin-3-yl)oxyJ-6-fluorophenyl }propan-2-ol, (0144) 4-(2-chloro-4-fluorophenyl)-N- (2- fluorophenyl)- 1 ,3 -dimethyl- 1 H-pyrazol-5-amine, (0145) 4-(2-chloro-4-fluorophenyl)-N-(2,6- difluorophenyl)-l,3-dimethyl-l H-pyrazol-5-amine, (0146) 4-(2-chl.oro-4-fluorophenyl)-N-(2- chloro-6-fluorophenyl)- 1 ,3 -dimethyl- lH-pyrazol-5-amine, (0147) 4-(2-bromo-4-fluorophenyl)- N-(2-chloro-6-fluorophenyl)-l,3-dimethyl-lH-pyrazol-5-amine, (0148) N-(2-bromo-6- fluorophenyl)-4-(2-chloro-4-fluorophenyl)-l,3-dimethyl-lH-pyrazol-5-amine, (0149) 4-(2- bromo-4-fluorophenyl)-N-(2-bromophenyl)-l,3-dimethyl-lH-pyrazol-5-arnine, (O150) 4-(2- bromo-4-fluorophenyl)-N-(2-bronio-6-fluorophenyl)-l.,3-dimethyl-lH-pyrazol-5-amine, (0151 ) 4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)- 1 ,3-dimethyl- lH-pyrazol-5-amine, (0152) N- (2-bromophenyl)-4-(2-chloro-4- fluorophenyl)- 1 ,3-dimethyl- 1 H-pyrazol-5-amine, (0153) 4-(2- chloro-4-fluorophenyl)-N-(2-chlorophenyl)- 1 ,3 -dimethyl- lH-pyrazol-5-arnine, (0154) 4-(2- bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)- 1 ,3-dimethyl- lH-pyrazol-5-amine, (01 5) 4-(2- bromo-4-fluorophenyl)-N-(2-fluorophenyl)- 1 ,3-dimethyl- lH-pyrazol-5-amine, (0156) N'-(4- { 3- [ difluoromemyl)sulfanylJphenoxy}-2,5-dimemylphenyl)-N-emyl-N-memylimidoformamide, (0157) ' -(2,5-dimethyl-4- { 3 -[( 1 , 1 ,2,2-tetraf luoroethyl)sulfanyl]phenoxy }phenyl)-N-ethyl-N- methylimidoformamide, (0158) N'-(2,5-dimethyl-4- ( 3-[(2,2,2- trifluoroethyl)sulfanyl]phenoxy }phenyl)-N-ethyl-N-methylimidoformamide, (0159) N' -(2,5- dimethyl-4-{ 3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N- methylimidoformamide, (0160) N'-(2,5-dimethyl-4- { 3-
[(pentafluoroemyl)sulfanyl]phenoxy}phenyl)-N-emyl-N-memylimidoformamide, (0161) N'-(4- { [3-(difluoromethoxy)phenylJsulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidofonnamide, (0162) N'-(2,5-dimethyl-4- { [3-( 1, 1 ,2,2-tetrafluoroethoxy)phenyl] sulf anyl }phenyl)-N-ethyl-N- methylimidoformamide, (0163) N'-(2,5-dimethyl-4-{ [3-(2,2,2- trifluoroethoxy)phenyl] sulf anyl }phenyl)-N-emyl-N-memylimidoformamide, (0164) N'-(2,5- dimethyl-4- { [3-(2,2,3,3-tetrafluoropropoxy)phenyl J sulf an l ] phenyl )-N-ethyl-N- methylimidoformamide, (0165) N'-(2,5-dimethyl-4-{ [3-
(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-emyl-N-memylinu^ofomiamide, (0166) 2-[3,5- bis(difluoromemyl)- l H-pyrazol- l-yl]-l-[4-(4- { 5-[2-(prop-2-yn-l-yloxy)phenyl]-4,5-dihydro- l,2-oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanone, (0167) 2-[3,5-bis(difluoromethyl)- lH-pyrazol-l-yl]-l-[4-(4- { 5-[2-fluoro-6-(prop-2-yn-l -yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3- yl } - 1 ,3-thiazol-2-yl)piperidin- 1 -yl]ethanone, (0168) 2-[3 ,5-bis(difluoromethyl)- 1 H-pyrazol- 1 - yl]-l-[4-(4-{ 5-[2-chloro-6-(prop-2-yn-l-yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl}- l,3-thiazol- 2-yl)piperidin- 1 -yi]ethanone, (0169) 2- { 3- [2-( 1 - { [3 ,5-bis(difluoromethyl)- 1 H-pyrazol- 1 - yl]acetyl}piperidin-4-yl)-l ,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5-yl }phenyl
methanesulfonate, (O170) 2-{ 3-[2-(l-{ [3,5-bis(difluoromethyl)-lH-pyrazol-l- yl]acetyl ]piperidin-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro-l.,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (0171 ) 2-[3, 5-bis(difluoromethyl)-l H-pyrazol- l-yl]-l-[4-(4- { (5S)-5- {2-(prop- 2-yn-l-yloxy)phenyl]-4,5-dihydro-l ,2-oxazol-3-yl ] -l,3-thiazol-2-yl)piperidin-l-yl]ethanone, (0172) 2-[3,5-bis(difluoromethyl)-l H-pyrazol- l-yl]-l-[4-(4-{ (5R)-5-[2-(prop-2-yn-l- yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanone, (0173) 2- [3,5-bis(difluoromethyl)-l H-pyrazol- l-yl]-l-[4-(4-{ (5S)-5-[2-fluoro-6-(prop-2-yn- 1 - yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl}-l ,3-thiazol-2-yl)piperidin-l-yl]ethanone, (0174) 2- [3,5-bis(difluoromethyl)- IH-pyrazol- 1 -yl]- 1 -[4-(4- { (5R)-5-[2-fluoro-6-(prop-2-yn-l- yloxy)phenyl]-4,5-dmydro-l,2-oxazol-3-yl}- l,3-miazol-2-yl)piperidin-l-yl]ethanone, (0175) 2- [3 ,5-bis(difluoromethy 1)- 1 H-pyrazol- 1 -yl] - 1 - [4-(4 - { (5S)-5 - {2-chloro-6-(prop-2-yn- 1 - yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanone, (0176) 2- [3 ,5-bis(difluoromethyl)- IH-pyrazol - 1 -y 1] - 1 - [4-(4- { (5 R)-5-[2-chloro-6-(prop-2-yn- 1 - yloxy)phenyl]-4,5-dmydro-l,2-oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanone, (0177) 2- {(5S)-3-[2-(l-{ [3,5-bis(difluoromethyl)-lH-pyrazol-l -yl]acetyl}piperidin-4-yl)-l ,3-thi yl]-4,5-dihydro- l,2-oxazol-5-yl}phenyl methanesulfonate, (0178) 2-{(5R)-3-[2-(l- { [3,5- bis(difluoromethyl)- IH-pyrazol - 1 -yl]acetyl}piperidin-4-yl)- 1 ,3-thiazol-4-y] j -4,5-di ydro- 1 ,2- o azol- 5 -yl} phenyl methanesulfonate, (0179) 2-{(5S)-3-[2-(l-{ [3,5-bis(difluoromethyl)- IH- pyrazol- 1-yl] acetyl } piperidin-4-yl)- 1 ,3-thiazol-4-yl] -4,5-dihydro- l,2-oxazol-5-yl}-3- chlorophenyl methanesulfonate, (0180) 2-{ (5R)-3- [2-( !■-{ [3,5-bis(difluoromethyl)- 1 H-pyrazol- l-yl]acetyl}piperidin-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (0181 ) (3S,6S,7R,8R)-8-benzyl-3-{3-[(isobutyryloxy)methoxy]-4- methoxypicolinamido } -6-methyl-4,9-dioxo- 1 ,5-dioxonan-7-yl isobutyrate.
As described above the compound of formula (I) can be mixed with one or more active compatible compound selected from insecticides/acaricides/neniaticides class, which are specified herein by their common names that are known and described, for example in The Pesticide Manual 17 th Ed., or can be searched in the internet (e.g. under www.alanwood.net/pesticides).
(.1 ) Acetylcholinesterase (AChE) inhibitors such as carbamates, for example alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxira, butoxycarboxim, carbaryl, carbofuran, carbosuifan, ethiofencarb, fenobucarb. forrnetanate, f rathiocarb, isoprocarb, metliiocarb. methomyl, metoicarb, oxamyl, pirimicarb, propoxur, tliiodicarb, thiofanox, triazamate, trimethaearb, XMC and xyiylcarb or organophosphates, such as acephate, azamethiphos, azinphos-ethyl, azinphos- methyl, cadusafos, chloreiboxyfos, chlorfenvinphos, chiormephos, chiorpyrifos, ehlorpyrifos- methyl, coumaphos, cyanophos, demeton-S-meihyl, diazinon, dichlorvos / DDVP, dicrolophos, dimethoate, dimethy!vinphos, disulfoton, EPN, etbion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O- (melhoxyan inothio-plKisphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocroto h s, naled, omethoate, oxydemeton-methyl, parathion, parathion-rneihyl, phentboate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methy!, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthioii, quinaiphos, sulfoiep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon and vamidoihion,
(2) GABA-gated chloride channel antagonists, such as cyclodiene organodiioriiies, for example chlordaiie and endosulfan or pbenvlpvrazoles (fiproles), for example ethiproie and fiproni!.
(3) Sodium channel modulators/voltage-dependent sodium channel blockers, such as pyretfcroids, for example acrinathrin, allethrin, d-cis-trans allethrin, d- trans allethrin, bifenthrin, bioal!ethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfl.uih.rin, bela-cyfl.uih.rin, eyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypem ethrin, beta- c yperi nethrin , theta-c y ermeihrin, zeia-cypermeihrin , eyphenofhrin [( 1R )-tn ms-\ some s] , deliamethri.n, empen hrin [(EZ)-(lR)-isomers], esfenvaierate, eiofenprox, fenpropathrin, fenvalerate, fiucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprolhrin, kadethrin, mo fluorothriii, permethrin, phenofhriii [( lR /ra/iy--isomer), prallethrin, pyrethrins ί pyretbrum), resmetlirin, silafluofen, tefluihrin, ietramethrin, tetrametlirm [(IR)-isomers)], tralomedirin and iransfiuthrin or DDT or methoxvchior.
(4) Nicotinic acetylcholine receptor (rs.ACbR) competitive modulators, such as neonicotinoids, for example acetamiprid, elothiaiiidin, dinotefuran, imidacloprid, niteiipyram, thiacloprid and iliia.mer.liox am or nicotine or sulfoxaflor or Oupyradi urone.
(5) Nicotinic acetylcholine receptor (nACliR) allosteric modulators, such as spinosyns, for example spinetoram and spiiiosad. (6) Glutamate-gaied chloride channel (GluCl) allosteric modulators, such as avennectins / milbemycins, for example abamectin, emamectin benzoate, lepimeciin and milbemectin,
(7) Juvenile hormone mimics such as juvenile hormone analogues, for example hydroprene, kinoprene and meth prene or fenoxycarb or pyriproxyfen.
(8) Active compounds with unknown or non-specific mechanisms of action, such as alkyl halides for example as methyl bromide and other alkyl halides or chloropicrin or fluorides or borates or tartar emetic or methyl isocyanate generators. (9) Chordotonai organ TRPV channel modulators such as pyridine azomethine derivatives, for example pyme rozine and pyrifluquinazon or flonicamid,
(10) Mite growth inhibitors, for example clofentezine, hexylhiazox and diflovidazin or etoxazole.
(11) Microbial disrupters of insect gut midgut, for example Bacillus thuringiensis subspecies israelensis. Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki. Bacillus thuringiensis subspecies tenehrionis and Bacillus sphaericus and BT crop proteins: CrylAb, CrvlAc, CrvlFa, CrylA 105, Cry2Ab, Vip3a, mCrySA, Cry3Ab, Cry3Bb, Cry34Abl / Cry35Abl.
(12) Inhibitors of mitochondrial ATP synthase such as organodn miticides, for example azocyelotin, cyhexatin and fenbutatin oxide or diafentliiuron or propargite or tetradifon.
(13) Uneoupiers of oxidative phosphorylation acting via disruption of the proton gradient, for example chlorfenapyr, DNOC and sulfluramid.
(14) Nicotinic acetylcholine receptor (iiAChR) channel blockers, such as bensultap, eartap- hydrochloride, thiocyclam and thiosultap-sodium,
(15) Inhibitors of chit i biosynthesis, type 0, such as bistrifluoron, chlorfluazuron. difhibenzuron, fliicycioxiiron, fiufenoxuron, hexaflumuron, !ufenuron, novahiron, novifiumuron, teflubenzuroii and triflumuroii.
(16) Inhibitors of chitin biosynthesis, type 1. such as buprofezin,
(17) Molting disrupters (particularly in Dipteran), such as cyromazine, (18) Ecclysone receptor agonists, such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide.
(19) Octopamine receptor agonists, such as amitraz. (20) Mitochondrial complex III electron transport inhibitors such as hydramethyinon or acequinocyl or fluacrypyrim or bifenazate.
(21) Mitochondria] comple I electron transport inhibitors, for example, MET! acarieides and insecticides, for example fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad or rotenone (Derris).
(22) Voltage-dependent sodium channel blockers such as indoxacarb or metaflumizone.
(23) inhibitors of acetyl CoA carboxylase, such as tetronic and tetramic acid derivatives, for example spirodiclofen, spiromesifen and spirotetramat.
(24) Mitochondrial complex IV electron transport Inhibitors, such as phosphides, for example aluminum phosphide, calcium phosphide, zinc phosphide and phosphlne or cyanides. (25) Mitochondrial complex II electron transport Inhibitors such as heta-ketonilrlle derivatives, for example cyeiiopyrafen and eyflumetofen or carboxanilides.
(28) Ryanodine receptor modulators such as diamides, for example chlorantramli prole, eyantraniliprole and fiubendiamicle.
(29) Chordotonal organ modulators on undefined target site such as flonicamid.
Further active ingredients with unknown or indeterminate mode of action, such as afidopyropen. afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, chinomethionat, cryolite, cycianillprole, eyeloxaprid, cyhalodiamide, dicloromezodaz, dieofol, dlflovidazin, flometoquin, fi uazaindolizine, lluensulibiie, flufeiierim, ilufenoxystrobin, flufiprole, fluhexafon, fluopyram, fluralaner, fluxametamide, fufenozide. guadipyr, heptafiuthrin, irnldac otliiz, iprodlone, lotilaner, meperfluthriii, paichongdiiig, pyflubumide, pyridaly , pyrifhiquinazon, pyriminostrobin, sarolaner, tetramethylftuthrin, tetraniliprole, tetrachlorantraniliprole, tioxazafeii, trifluraezopyrim and iodomethane; iiirthermore, preparations based on Bacillus firtnus (1-1582, BioNeem, Votivo), and the following known active compounds: l- { 2-fluoiO~4~meihyI-5-[(2,2,2 ^^
l -l,2,4-triazol-5-amine (known from WO2006043635), { r- [(2E) -3 -(4-chloiOphenyl)prop -2- ene-] -yl]~5~fiuorospiro[mdole-3,4^
(known from WO2003106457), 2-chioro-N-i2- ( 1 -[(2E)-3-( 4-chloropheny 1 )prop-2-en- 1- yl]piperidin-4-yl}-4-(trifluoromeihyl)phenyl]isotiicoim (known from WO2006003494), 3- (2,5"diniethylphenyl)"4-'hydroxy'-8-methoxy-l,8'-diazaspiro[4.5]dec-3"en--2-one (known from WO2009049851), 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-l,8-diaz.aspiro[4.5]dec-3-en-4-yl ethylcarbonate (known from W()2i)09049851 ), 4-(but-2-in- 1 -yloxy)-6-(3,5-dimethylpiperidin-l- yiyS-fluoropyrimidme (known from WO2004099I60), 4-(but-2-in-l-yloxy)-6-(3- cMorophenyDpyrimidine (known from WO2003076415), PF.1364 (CAS-Reg. o. 1204776-60- 2), methyl --2-- [2- ({ [3-bromo- l ~(3--chloropyridiii"2-y!)-i H" yra ol■ "yl]c rboI1yl} m no)■■5■■ chloro-3-mε·ίh"ylbenzo ] j-2-meilrylbydrazincarboxylate (known from WO200508521 ), inetiiy!- 2-i2"({ [3-bromo-l"(3-chloropyTidin"2- l) H"p Tazol"5"yl]carbonyl}amino)-5"CyaiiO"3- niel ylbenzijylj-2-eihylhydrazincarboxylate (known from WO2005085216), meihyl-2-[ 2-( { [3- bromo- 1 -(3-chloro-pyridin-2-yl)- ί H-pyrazoi-5-yljcarbonyi } amino)- 5 -cyano-3-methylbenzoyl] ·- 2~memy}hydrazmcarboxylaie (known from WO2005085216), meihyl-2-[3,5-dibromo-2-({ i3- bronui-l-(3-chk)ro-pyndin-2-yl)-lH-pyrazol-5-yl]carbonyl}aniiiKi)benzoyi]-2- ethylhydrazincarboxylate (known from WO2005085216), N-[2-(5-amino-l,3,4-tliiadiazol-2-yl)- 4-ch!oro-6-methyiphenyi]-3-broino-l.-(3-chloropyridin-2-yl)-l H-pyrazoie-5-carbox
(known from CN102057925), 4-[5-(3,5-dicMorophenyl)-5-(irifluoromethyl)-4,5-dihydiO-l,2- oxazol-3-yl]-2-methy!-N-(l-oxidothietan-3-yl)benzamide (known from WO2009080250), N- [(2E)-l-[(6-chloropyiidine~3-yl)mediyl]pyridin-2(lH (known from WO2012029672), l.-[(2-chkm l,3-thiazo]-5-yl)meaiyl3-4-oxo-3-phenyl-4H-pyrido[l,2- ajpyrimidin - 1 -iurn■ -olaie (known from WO2009099929), 1■■ [(6 -chloropyridin -3 - yl) ethyl] -4- oxo-3-phenyl-4H-pyrido[].,2-a]pyrimidin-l-ii3rn-2-o]ate (known from WO2009099929), < - {2,6"dich!orO"4 (3,3-dichloroprop"2-en-l-yl)oxy]pheiioxy}propoxy)--2--meilioxy-6"
(irifluoromediyl)pyrimidine (known from CN101337940), N-[2-(ie?f-butylcarbamoyl)-4-chloro- 6-methylphenyl]■■ 1 -(3-chloropyridin- 2■ yl)■ 3 -(fluoromethoxy)-- 1 H -pyrazole- 5 -carboxamide (known from WO2008134969), butyl-[2-(2,4-dichlorophenyl)-3-oxo-4-oxaspiro[4.5]dec-l-en-l- yljcarbonate (disclosed in CN102060818), 3(E)-3-[1.-[(6-chlox -3-pyridyl)mediyl]-2- pyridyliden]-l,l,l-trifluoropropan-2-one (known from WO2013144213), N-(methylsulfonyl)-6- [2-(pyridin-3-yl)-l,3-thiazol-5-yl]pyridirje-2-carboxamide (known from WO2012000896), N-[3- (benzylcarbamoyl)--4-chlorophenyl] -l--nieihyl--3"(peniafluoroeiliyl)-4--(trifluoromeihyl)-lH- pyrazole-5-carboxamide (known from WO20.10051926).
The compounds of formula (I) may be used to treat several fungal pathogens. Non-limiting examples of pathogens of fungal diseases which can be treated in accordance with the invention include: diseases caused by powdery mildew pathogens, for example Blumeria species, for example
Blumeria graminis; Podosphaera species, for example Podosphaera leucotricha; Sphaerotheca species, for example Sphaerotheca fuliginea; Uncinuia species, for example Uncinuia necator; Erysiphe species, for example Erysiphe dehor ac earn:
diseases caused by rust disease pathogens, for example Gymnosporangium species, for example Gymnosporangium sabinae; Hemileia species, for example Hemileia vastatrix; Phakopsora species, for example Phakopsora pachyrhizi or Phakopsora meihomiae; Puccinia species, for example Puccinia recondita, Puccinia graminis oder Puccinia striiformis; Uromyces species, for example Uromyces appendiculatus ;
diseases caused by pathogens from the group of the Oomycetes, for example Albugo species, for example Albugo Candida; Bremia species, for example Bremia lactucae; Peronospora species, for example Peronospora pisi or P. brassicae; Phytophthora species, for example Phytophthora infestans; Plasmopara species, for example Plasmopara viticola; Pseudoperonospora species, for example Pseudoperonospora humuli or Pseudoperonospora cubensis; Pythium species, for example Pythium ultimum;
leaf blotch diseases and leaf wilt diseases caused, for example, by Aiiernaria species, for example Alternaria solani; Cercospora species, for example Cercospora beticola; Cladiosporium species, for example Cladiosporium, cucumerinum,; Cochliobolus species, for example Cochliobolus sativus (conidial form: Drechslera, syn: Helminthosporium) or Cochliobolus miyabeanus; Colletoirichum species, for example Colletoirichum lindemuthanium; Cycloconium species, for example Cycloconium oleaginum; Diaporthe species, for example Diaporthe citri Elsinoe species, for example Elsinoe fawcettii; Gloeosporium species, for example Gloeosporium laeticolor; Glomerella species, for example Glomerella cingulata; Guignardia species, for example Guignardia bidwelli; Leptosphaeria species, for example Leptosphaeria maculans; Magnaporlhe species, for example Magnaporthe grisea; Microdochium species, for example Microdochium. nivale; Mycosphaerella species, for example Mycosphaerella graminicola, Mycosphaerella arachidicola or Mycosphaerella fijiensis; Phaeosphaeria species, for example Phaeosphaeria nodoruni; Pyrenophora species, for example Pyrenophora teres or Pyrenophora tritici repenlis; Ramularia species, for example Ramularia collo-cygni or Ramularia areola: Rhynchosporium species, for example Rhynchosporium secalis; Septoria species, for example Septoria apii or Septoria lycopersici; Stagonospora species, for example Stagonospora nodorum; Typhula species, for example Typhula incarnata; Venturia species, for example Venturia inaequalis;
root and stem diseases caused, for example, by Corticium species, for example Corticium graminearum; Fusarium species, for example Fusarium oxysporum; Gaeumannomyces species, for example Gae niannomyces graminis; Plasmodiophora species, for example Plasmodiophora brassicae; Rhizoctonia species, for example Rhizoctonia solani; Sarocladium species, for example Sarocladium oryzae; Sclerotium species, for example Sclerotium oryzae; Tapesia species, for example Tapesia acuformis; Thielaviopsis species, for example Thielaviopsis basicola; Ganoderrna species, for example Ganoderrna lucidum;
ear and panicle diseases (including corn cobs) caused, for example, by Alternaria species, for example Alternaria spp.; Aspergillus species, for example Aspergillus flavus; Cladosporium species, for example Cladosporium cladosporioides; Claviceps species, for example Claviceps purpurea; Fusarium species, for example Fusarium culmorum; Gibberella species, for example Gibberella zeae; Monographella species, for example Monographella nivalis; Stagnospora species, for example Stagnospora nodorum;
diseases caused by smut fungi, for example Sphacelotheca species, for example Sphacelotheca reiliana; Tilletia species, for example Tilletia caries or Tilletia controversa; Urocystis species, for example Urocystis occulta; Ustilago species, for example Uslilago nuda;
fruit rot caused, for example, by Aspergillus species, for example Aspergillus flavus; Botrytis species, for example Botrytis cinerea; Penicillium species, for example Penicilliurn expansum or Penicillium purpurogenum; Rhizopus species, for example Rhizopus stolonifer; Sclerotinia species, for example Sclerotinia sclerotiorum; Verticilium species, for example Verticilium alboatrum;
seed- and soil-borne rot and wilt diseases, and also diseases of seedlings, caused, for example, by Alternaria species, for example Alternaria brassicicola; Aphanomyces species, for example Aphanomyces euteiches; Ascochyta species, for example Ascochyta lends; Aspergillus species, for example Aspergillus flavus; Cladosporium species, for example Cladosporium herbarum; Cochliobolus species, for example Cochliobolus sativus (conidial form: Drechslera, Bipolaris Syn: Helminthosporium); Colletotrichurn species, for example Colletotrichum coccodes; Fusarium species, for example Fusarium culmorum Gibberella species, for example Gibberella zeae; Macrophomina species, for example Macrophomina phaseolina; Microdochiurn species, for example Microdochiurn nivale: Monographella species, for example Monographella nivalis; Penicillium species, for example Penicilliurn expansum; Phoma species, for example Phoma lingam; Phomopsis species, for example Phomopsis sojae; Phytophthora species, for example Phytophthora cactorum; Pyrenophora species, for example Pyrenophora graminea; Pyricularia species, for example Pyricularia oryzae; Pythium species, for example Pythium ultimum; Rhizoctonia species, for example Rhizoctonia solani; Rhizopus species, for example Rhizopus oryzae; Sclerotium species, for example Sclerotium rolfsii; Septoria species, for example Septoria nodorum; Typhula species, for example Typhula incamata; Verticillium species, for example Verticillium dahliae;
cancers, galls and witches' broom caused, for example, by Nectria species, for example Nectria galligena:
wilt diseases caused, for example, by MonUinia species, for example Monilinia laxa;
deformations of leaves, flowers and fruits caused, for example, by Exobasidium species, for example Exobasidium vexans; Taphrina species, for example Taphrina deformans;
degenerative diseases in woody plants, caused, for example, by Esca species, for example Phaeomoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranea; Ganoderma species, for example Ganoderma boninense;
diseases of flowers and seeds caused, for example, by Botrytis species, for example Botrytis cinerea;
diseases of plant tubers caused, for example, by Rhizoctonia species, for example Rhizoctonia solani; Helminthosporium species, for example Helminthosporium solani;
diseases caused by bacterial pathogens, for example Xanthomonas species, for example Xanthomonas carnpestris pv. oryzae; Pseudomonas species, for example Pseudomonas syringae /;·! . lachrymans; Erwinia species, for example Erwinia amylovora Ralstonia species, for example Ralstonia solanacearum;
Fungal diseases on roots and the stem base caused, for example, by black root rot (Calonectria crotalariae), charcoal rot (Macrophomina phaseolina), fusarium blight or wilt, root rot, and pod and collar rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), mycoleptodiscus root rot (Mycoleptodiscus terrestris), neocosmospora (Neocosmospora vasinfecta), pod and stem blight (Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var. caulivora), phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophora gregatd), pythium rot (Pythium aphaniderrnaium, Pythiurn irregulare, Pythium deharyanum, Pythium myrioiyium, Pythium ultimuni), rhizoctonia root rot, stem decay, and damping-off (Rhizoctonia solani), sclerotinia stem decay (Sclerotinia sclerotiorum), sclerotinia southern blight (Sclerotinia roljsii), thielaviopsis root rot (Thielaviopsis basicola).
The compounds of formula (I) are especially useful for the control of nematodes. Thus, in a further aspect, the invention also relates to a method of controlling damage to plant and parts thereof by plant parasitic nematodes (Endoparasitic, Semiendoparasitic and Ectoparasitic nematodes), especially plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne arenaria and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Glohodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoid.es species; Sting nematodes, Eelonolaimus longicaudatus and other Belonolaimus species; Pine nematodes, Bursaphelenchus xylophilus and other Burs aphelenchus species; Ring nematodes, Criconenia species, Criconemella species, Criconemoides species, Mesocriconema species; Stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus species; Awl nematodes, Dolichodorus species; Spiral nematodes, Heliocot lenchus multicinctus and other Helicotylenchus species; Sheath and sheathoid nematodes, Hemicycliophora species and Hemicriconemoides species; Hirshntanniella species; Lance nematodes, Hoploaimus species; false rootknot nematodes, Nacobbus species; Needle nematodes, Longidorus elongatus and other Longidorus species; Pin nematodes, Pratylenchus species; Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species; Burrowing nematodes, Radopholus similis and other Radopholus species; Reniform nematodes, Rotylenchus robuslus, Rotylenchus reniformis and other Rotylenchus species; Scutellonema species; Stubby root nematodes, Trichodorus primitivus and other Trichodorus species, Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species; Citrus nematodes, Tylenchulus species; Dagger nematodes, Xiphinema species; and other plant parasitic nematode species, such as Subanguina spp., Hypsoperine spp., Macroposthonia spp., Melinius spp., Punctodera spp., and Quinisulcius spp.. Particularly, the nematode species Meloidogyne spp., Heterodera spp., Rotylenchus spp. and Pratylenchus spp. can be controlled by compounds of the present invention.
Plants which can be treated in accordance with the invention include the following: Rosaceae sp (for example pome fruits such as apples, pears, apricots, cherries, almonds and peaches), Rihesioidae sp.,
Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp.,
Actinidaceae sp., Lauraceae sp., Musaceae sp. (for example banana trees and plantations),
Rubiaceae sp. (for example coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (for example lemons, oranges and grapefruit); Vitaceae sp. (for example grapes); Solanaceae sp. (for example tomatoes, peppers), Liliaceae sp., Asteraceae sp. (for example lettuce), Umbelliferae sp., Cr ciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (for example cucumber), Alliaceae sp. (for example leek, onion), Papilionaceae sp. (for example peas); major crop plants, such as PoaceaeiGramineae sp. (for example maize, turf, cereals such as wheat, rye, rice, barley, oats, millet and triticale),
Asteraceae sp. (for example sunflower), Brassicaceae sp. (for example white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, and oilseed rape, mustard, horseradish and cress), Fabacae sp. (for example bean, peanuts), Papilionaceae sp. (for example soya bean), Solanaceae sp. (for example potatoes), Chenopodiaceae sp. (for example sugar beet, fodder beet, swiss chard, beetroot); Malvaceae (for example cotton); useful plants and ornamental plants for gardens and wooded areas; and genetically modified varieties of each of these plants.
Ail plants and plant parts can be treated in accordance with the invention. Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plan cultivars which are protectable and non-protectable by plant breeders' rights. Plant parts are understood to mean all parts and organs of plants above and below the ground, such as shoot, leaf, flower and root, examples of which include leaves, needles, stalks, stems, flowers, fruit bodies, fruits and seeds, and also roots, tubers and rhizomes. The plant parts also include harvested material and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, slips and seeds.
The invention furthermore includes a method for treating seed, particularly seeds (dormant, primed, pregerminated or even with emerged roots and leaves) treated with at least one of the compounds of the formula (I) and compositions thereof. The inventive seeds are used in methods for protection of seeds and emerged plants from the seeds from phytopathogenic harmful fungi. In these methods, seed treated with at least one inventive active ingredient is used.
It is also desirable to optimize the amount of the active ingredient used so as to provide the best possible protection for the seeds, the germinating plants and emerged seedlings from attack by phytopathogenic fungi, but without damaging the plants themselves by the active ingredient used. In particular, methods for the treatment of seed should also take into consideration the intrinsic phenotypes of transgenic plants in order to achieve optimum protection of the seed and the germinating plant with a minimum of crop protection compositions being employed. The present invention therefore also relates to a method for protecting seeds, germinating plants and emerged seedlings against attack by animal pests, nematodes and/or phytopathogenic harmful microorganisms by treating the seeds with an inventive composition. The invention also relates to the use of the compositions according to the invention for treating seeds for protecting the seeds, the germinating plants and emerged seedlings against animal pests and/or phytopathogenic microorganisms. The invention further relates to seeds which have been treated with an inventive composition for protection from animal pests and/or phytopathogenic microorganisms ,
One of the advantages of the present invention is that the treatment of the seeds with these compositions not only protects the seed itself, but also the resulting plants after emergence, from animal pests and/or phytopathogenic harmful microorganisms. In this way, the immediate treatment of the crop at the time of sowing or shortly thereafter protect plants as well as seed treatment in prior to sowing. It is likewise considered to be advantageous that the inventive active ingredients or compositions can be used especially also for transgenic seed, in which case the plant which grows from this seed is capable of expressing a protein which acts against pests, herbicidal damage or abiotic stress. The treatment of such seeds with the inventive active ingredients or compositions, for example an insecticidal protein, can result in control of certain pests.
The compounds of the formula (I) are suitable for protection of seed of any plant variety which is used in agriculture, in the greenhouse, in forests or in horticulture. More particularly, the seed is that of cereals (such as wheat, barley, rye, millet and oats), oilseed rape, maize, cotton, soybeen, rice, potatoes, sunflower, beans, coffee, beet (e.g. sugar beet and fodder beet), peanut, vegetables (such as tomato, cucumber, onions and lettuce), lawns and ornamental plants. Of particulai- significance is the treatment of the seed of wheat, soybean, oilseed rape, maize and rice.
As also described below, the treatment of transgenic seed with the inventive active ingredients or compositions is of particular significance. This refers to the seed of plants containing at least one heterologous gene which allows the expression of a polypeptide or protein, e.g. having insecticidal properties. These heterologous genes in transgenic seeds may originate, for example, from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavihacter, Glomus or Gliodadium. These heterologous genes preferably originate from Bacillus sp., in which case the gene product is effective against the European corn borer and/or the Western com rootworm. Particularly preferably, the heterologous genes originate from Bacillus thuringiensis . In the context of the present invention, the inventive composition is applied to seeds either alone or in a suitable formulation. Preferably, the seed is treated in a state in which it is sufficiently stable for no damage to occur in the course of treatment. In general, seeds can be treated at any time between harvest and some time after sowing. It is customary to use seed which has been separated from the plant and freed from cobs, shells, stalks, coats, hairs or the flesh of the fruits. For example, it is possible to use seed which has been harvested, cleaned and dried down to a moisture content of less than 15% by weight. Alternatively, it is also possible to use seed which, after drying, for example, has been treated with water and then dried again, or seeds just after priming, or seeds stored in primed conditions or pre-germinated seeds, or seeds sown on nursery trays, tapes or paper.
When treating the seeds, it generally has to be ensured that the amount of the inventive composition applied to the seed and/or the amount of further additives is selected such that the germination of the seed is not impaired, or that the resulting plant is not damaged. This must be ensured particularly in the case of active ingredients which can exhibit phvtotoxic effects at certain application rates.
The compounds of the formula (I) can be applied directly, i.e. without containing any other components and without having been diluted. In general, it is preferable to apply the compositions to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art.
The compounds of the formula (I) can be converted to the customary formulations relevant to on-seed applications, such as solutions, emulsions, suspensions, powders, foams, slurries or combined with other coating compositions for seed, such as film forming materials, pelleting materials, fine iron or other metal powders, granules, coating material for inactivated seeds, and also ULV formulations.
In the treatment of seeds to facilitate plantability seeds can be coated with polymer. The polymer coating is comprised of a binder, a wax and a pigment, and one or more stabilizers in an amount effective to stabilize the suspension. The binder can be a polymer selected from the group consisting of vinyl acetate-ethylene copolymer, vinyl acetate homopolymer, vinyl acetate-acrylic copolymer, vinylacrylic, acrylic, ethylene-vinyl chloride, vinyl ether maleic anhydride, or butadiene styrene. Other similar polymers can be used.
These formulations are prepared in a known manner, by mixing the active ingredients or active ingredient combinations with customary additives, for example customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, adhesives, gibberellins, and also water.
Useful dyes which may be present in the seed dressing formulations usable in accordance with the invention are all dyes which are customary for such purposes. It is possible to use either pigments, which are sparingly soluble in water, or dyes, which are soluble in water. Examples include the dyes known by the names Rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red I.
Useful wetting agents which may be present in the seed dressing formulations usable in accordance with the invention are all substances which promote wetting and which are conventionally used for the formulation of active agrochemical ingredients. Usable with preference are alkylnaphthaienesuiphonates, such as diisopropyl- or diisobutylnaphthalenesulphonates.
Useful dispersants and/or emulsifiers which may be present in the seed dressing formulations usable in accordance with the invention are all nonionic, anionic and cationic dispersants conventionally used for the formulation of active agrochemical ingredients. Usable with preference are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Useful nonionic dispersants include especially ethylene oxide/propylene oxide block polymers, alkylphenol poiygiycol ethers and tristryrylphenol polyglycol ether, and the phosphated or sulphated derivatives thereof. Suitable anionic dispersants are especially lignosulphonates, polyacrylic acid salts and arylsulphonate/formaldehyde condensates.
Antifoams which may be present in the seed dressing formulations usable in accordance with the invention are all foam-inhibiting substances conventionally used for the formulation of active agrochemical ingredients. Silicone antifoams and magnesium stearate can be used with preference.
Preservatives which may be present in the seed dressing formulations usable in accordance with the invention are all substances usable for such purposes in agrochemical compositions. Examples include dichiorophene and benzyl alcohol hemiformal.
Secondary thickeners which may be present in the seed dressing formulations usable in accordance with the invention are all substances usable for such purposes in agrochemical compositions. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
Adhesives which may be present in the seed dressing formulations usable in accordance with the invention are all customary binders usable in seed dressing products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose. The formulations for on-seed applications usable in accordance with the invention can be used to treat a wide variety of different kinds of seed either directly or after prior dilution with water. For instance, the concentrates or the preparations obtainable therefrom by dilution with water can be used to dress the seed of cereals, such as wheat, barley, rye, oats, and triticale, and also seeds of maize, soybean, rice, oilseed rape, peas, beans, cotton, sunflowers, and beets, or else a wide variety of different vegetable seeds. The formulations usable in accordance with the invention, or the dilute preparations thereof, can also be used for seeds of transgenic plants. In this case, additional effects may also occur in interaction with the substances formed by expression.
For treatment of seeds with the formulations usable in accordance with the invention, or the preparations prepared therefrom by adding water, all mixing units usable customarily for on-seed applications are useful. Specifically, the procedure in on-seed applications is to place the seeds into a mixer, to add the particular desired amount of the formulations, either as such or after prior dilution with water, and to mix everything until all applied formulations are distributed homogeneously on the seeds. If appropriate, this is followed by a drying operation.
The application rate of the formulations usable in accordance with the invention can be varied within a relatively wide range. It is guided by the particular content of the active ingredients in the formulations and by the seeds. The application rates of each single active ingredient are generally between 0.001 and 15 g per kilogram of seed, preferably between 0.01 and 5 g per kilogram of seed.
When using the compounds of the formula (I) as fungicides, the application rates can be varied within a relatively wide range, depending on the kind of application. The application rate of the inventive active ingredients is: in the case of treatment of plant parts, for example leaves: from 0.1 to 10000 g ha, preferably from 10 to 1000 g/ha, more preferably from 30 to 300 g/ha (in the case of application by watering or dripping, it is even possible to reduce the application rate, especially when inert substrates such as rockwool or perlite are used); in the case of seed treatment: from 0.1 to 10 kg per 100 kg of seed, preferably from 1 to 150 g per 100 kg of seed, more preferably from 2.5 to 25 g per 100 kg of seed, even more preferably from 2.5 to 12.5 g per 100 kg of seed; in the case of soil treatment: from 0.1 to 10000 g/ha, preferably from 1 to 5000 g/ha.
These application rates are merely by way of example and are not limiting for the purposes of the invention.
In some cases, the compounds of the formula (I) can, at particular concentrations or application rates, also be used as herbicides, safeners, growth regulators or agents to improve plant properties, or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including compositions against yiroids) or as compositions against MLO (Mycoplasma-like organisms) and RLO (Rickettsia- like organisms).
The compounds of the formula (I) intervene in physiological processes of plants and can therefore also be used as plant growth regulators. Plant growth regulators may exert various effects on plants. The effect of the substances depends essentially on the time of application in relation to the developmental stage of the plant, the plant variety and also on the amounts of active ingredient applied to the plants or their environment and on the type of application. In each case, growth regulators should have a particular desired effect on the crop plants.
Growth regulating effects, comprise earlier germination, better emergence, more developed root system and/or improved root growth, increased ability of tillering, more productive tillers, earlier flowering, increased plant height and/or biomass, shorting of stems, improvements in shoot growth, number of kernels/ear, number of ears/m2, number of stolons and/or number of flowers, enhanced harvest index, bigger leaves, less dead basal leaves, improved phyliotaxy, earlier maturation/ earlier fruit finish, homogenous riping, increased duration of grain filling, better fruit finish, bigger fruit/vegetable size, sprouting resistance and reduced lodging.
Increased or improved yield is referring to total biomass per hectare, yield per hectare, kernel/fruit weight, seed size and/or hectolitre weight as well, as to improved product quality, comprising:
improved processability relating to size distribution (kernel, fruit, etc.), homogenous riping, grain moisture, better milling, better vinification, better brewing, increased juice yield, harvestability, digestibility, sedimentation value, falling number, pod stability, storage stability, improved fiber length/strength/uniformity, increase of milk and/or meet quality of silage fed animals, adaption to cooking and frying;
further comprising improved marketability relating to improved fruit/grain quality, size distribution (kernel, fruit, etc.), increased storage/shelf-life, firmness /softness, taste (aroma, texture, etc.), grade (size, shape, number of berries, etc.), number of berries/fruits per bunch, crispness, freshness, coverage with wax, frequency of physiological disorders, colour, etc.:
further comprising increased desired ingredients such as e.g. protein content, fatty acids, oil content, oil quality, aminoacid composition, sugar content, acid content (pH), sugar/acid ratio (Brix), polyphenols, starch content, nutritional quality, gluten content/index, energy content, taste, etc.;
and further comprising decreased undesired ingredients such as e.g. less mycotoxines, less aflatoxines, geosmin level, phenolic aromas, lacchase, polyphenol oxidases and peroxidases, nitrate content etc. Plant growth-regulating compounds can be used, for example, to slow down the vegetative growth of the plants. Such growth depression is of economic interest, for example, in the case of grasses, since it is thus possible to reduce the frequency of grass cutting in ornamental gardens, parks and sport facilities, on roadsides, at airports or in fruit crops. Also of significance is the inhibition of the growth of herbaceous and woody plants on roadsides and in the vicinity of pipelines or overhead cables, or quite generally in areas where vigorous plant growth is unwanted.
Also important is the use of growth regulators for inhibition of the longitudinal growth of cereal. This reduces or completely eliminates the risk of lodging of the plants prior to harvest. In addition, growth regulators in the case of cereals can strengthen the culm, which also counteracts lodging. The employment of growth regulators for shortening and strengthening culms allows the deployment of higher fertilizer volumes to increase the yield, without any risk of lodging of the cereal crop. In many crop plants, vegetative growth depression allows denser planting, and it is thus possible to achieve higher yields based on the soil surface. Another advantage of the smaller plants obtained in this way is that the crop is easier to cultivate and harvest.
Reduction of the vegetative plant growth may also lead to increased or improved yields because the nutrients and assimilates are of more benefi to flower and fruit formation than to the vegetative parts of the plants.
Alternatively, growth regulators can also be used to promote vegetative growth. This is of great benefit when harvesting the vegetative plant parts. However, promoting vegetative growth may also promote generative growth in that more assimilates are formed, resulting in more or larger fruits,
Furthermore, beneficial effects on growth or yield can be achieved through improved nutrient use efficiency, especially nitrogen (N)-use efficiency, phosphours (P)-use efficiency, water use efficiency, improved transpiration, respiration and/or C02 assimilation rate, better nodulation, improved Ca-metabolism etc.
Likewise, growth regulators can be used to alter the composition of the plants, which in turn may result in an improvement in quality of the harvested products. Under the influence of growth regulators, parthenocarpic fruits may be formed. In addition, it is possible to influence the sex of the flowers. It is also possible to produce sterile pollen, which is of great importance in the breeding and production of hybrid seed. Use of growth regulators can control the branching of the plants. On the one hand, by breaking apical dominance, it is possible to promote the development of side shoots, which may be highly desirable particularly in the cultivation of ornamental plants, also in combination with an inhibition of growth. On the other hand, however, it is also possible to inhibit the growth of the side shoots. This effect is of particular interest, for example, in the cultivation of tobacco or in the cultivation of tomatoes.
Under the influence of growth regulators, the amount of leaves on the plants can be controlled such that defoliation of the plants is achieved at a desired time. Such defoliation plays a major role in the mechanical harvesting of cotton, but is also of interest for facilitating harvesting in other crops, for example in viticulture. Defoliation of the plants can also be undertaken to lower the transpiration of the plants before they are transplanted.
Furthermore, growth regulators can modulate plant senescence, which may result in prolonged green leaf area duration, a longer grain filling phase, improved yield quality, etc. Growth regulators can likewise be used to regulate fruit dehiscence. On the one hand, it is possible to prevent premature fruit dehiscence. On the other hand, it is also possible to promote fruit dehiscence or even flower abortion to achieve a desired mass ("thinning"). In addition, it is possible to use growth regulators at the time of harvest to reduce the forces required to detach the fruits, in order to allow mechanical harvesting or to facilitate manual harvesting. Growth regulators can also be used to achieve faster or else delayed ripening of the harvested material before or after harvest. This is paiticulai y advantageous as it allows optimal adjustment to the requirements of the market. Moreover, growth regulators in some cases can improve the fruit colour. In addition, growth regulators can also be used to synchronize maturation within a certain period of time. This establishes the prerequisites for complete mechanical or manual harvesting in a single operation, for example in the case of tobacco, tomatoes or coffee.
By using growth regulators, it is additionally possible to influence the resting of seed or buds of the plants, such that plants such as pineapple or ornamental plants in nurseries, for example, germinate, sprout or flower at a time when they are normally not inclined to do so. in areas where there is a risk of frost, it may be desirable to delay budding or germination of seeds with the aid of growth regulators, in order to avoid damage resulting from late frosts.
Finally, growth regulators can induce resistance of the plants to frost, drought or high salinity of the soil. This allows the cultivation of plants in regions which are normally unsuitable for this purpose.
The compounds of the formula (I) also exhibit a potent strengthening effect in plants. Accordingly, they can be used for mobilizing the defences of the plant against attack by undesirable microorganisms.
Plant- strengthening (resistance-inducing) substances in the present context are substances capable of stimulating the defence system of plants in such a way that the treated plants, when subsequently inoculated with undesirable microorganisms, develop a high degree of resistance to these microorganisms. Further, in context with the present invention plant physiology effects comprise the following: Abiotic stress tolerance, comprising tolerance to high or low temperatures, drought tolerance and recovery after drought stress, water use efficiency (correlating to reduced water consumption), flood tolerance, ozone stress and UV tolerance, tolerance towards chemicals like heavy metals, salts, pesticides etc.
Biotic stress tolerance comprising increased fungal resistance and increased resistance against nematodes, viruses and bacteria. In context with the present invention, biotic stress tolerance preferably comprises increased fungal resistance and increased resistance against nematodes. Increased plant vigor, comprising plant health / plant quality and seed vigor, reduced stand failure, improved appearance, increased recovery after periods of stress, improved pigmentation (e.g. chlorophyll content, stay-green effects, etc.) and improved hoto synthetic efficiency.
In addition, the compounds of the formula (I) can reduce the mycotoxin content in the harvested material and the foods and feeds prepared therefrom. Mycotoxins include particulai y, but not exclusively, the following: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2- and HT2-toxin, fumonisins, zearalenon, moniliformin, fusarin, diaceotoxyscirpenol (DAS), beauvericin, enniatin, fusaroproliferin, fusarenol, ochratoxins, patulin, ergot alkaloids and aflatoxins which can be produced, for example, by the following fungi: Fusarium spec, such as F. acuminatum, F. asiaticum, F. avenaceum, F. crookwellense, F. culmorum, F. graminearum (Gibberella zeae), F. equiseti, F. fujikoroi, F. musarum, F. oxysporum, F. proliferatum, F. poae, F. pseudograminearum, F. sambucinum, F. scirpi, F. semitectum, F. solani, F. sporotrichoides, F. langsethiae, F. subglutincms, F. tricincium, F. verticillioides etc., and also by Aspergillus spec, such as A. flavus, A, parasiticus, A. nomius, A. ochraceus, A. clavatus, A. terreus, A. versicolor, Penicillium spec, such as P. verrucosum, P. viridicatum, P. citrinum, P. expansum, P. claviforme, P. roqueforti, Claviceps spec, such as C. purpurea, C. fusiformis, C. paspali, C. africana, Stachybotrys spec and others.
The compounds of the formula (I) can also be used in the protection of materials, for protection of industrial materials against attack and destruction by phytopathogenic fungi.
In addition, the compounds of the formula (I) can be used as antifouling compositions, alone or in combinations with other active ingredients. Industrial materials in the present context are understood to mean inanimate materials which have been prepared for use in industry. For example, industrial materials which are to be protected by- inventive compositions from microbial alteration or destruction may be adhesives, glues, paper, wallpaper and board/cardboard, textiles, carpets, leather, wood, fibers and tissues, paints and plastic articles, cooling lubricants and other materials which can be infected with or destroyed by microorganisms. Parts of production plants and buildings, for example cooling-water circuits, cooling and heating systems and ventilation and air-conditioning units, which may be impaired by the proliferation of microorganisms may also be mentioned within the scope of the materials to be protected. Industrial materials within the scope of the present invention preferably include adhesives, sizes, paper and card, leather, wood, paints, cooling lubricants and heat transfer fluids, more preferably wood.
The compounds of the formula (I) may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.
In the case of treatment of wood the compounds of the formula (I) may also be used against fungal diseases liable to grow on or inside timber. The term "timber" means all types of species of wood, and all types of working of this wood intended for construction, for example solid wood, high-density wood, laminated wood, and plywood. The method for treating timber according to the invention mainly consists in contacting a composition according to the invention; this includes for example direct application, spraying, dipping, injection or any other suitable means. In addition, the compounds of the formula (I) can be used to protect objects which come into contact with saltwater or brackish water, especially hulls, screens, nets, buildings, moorings and signalling systems, from fouling.
The compounds of the formula (I) can also be employed for protecting storage goods. Storage goods are understood to mean natural substances of vegetable or animal origin or processed products thereof which are of natural origin, and for which long-term protection is desired.
Storage goods of vegetable origin, for example plants or plant parts, such as stems, leaves, tubers, seeds, fruits, grains, can be protected freshly harvested or after processing by (pre)drying, moistening, comminuting, grinding, pressing or roasting. Storage goods also include timber, both unprocessed, such as construction timber, electricity poles and barriers, or in the form of finished products, such as furniture. Storage goods of animal origin are, for example, hides, leather, furs and hairs. The inventive compositions may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.
Microorganisms capable of degrading or altering the industrial materials include, for example, bacteria, fungi, yeasts, algae and slime organisms. The compounds of the formula (I) preferably act against fungi, especially moulds, wood-discoloring and wood-destroying fungi (Ascomycetes,
Basidiomycetes, Deuteromycetes and Zygomycetes), and against slime organisms and algae. Examples include microorganisms of the following genera: Altemaria, such as Alternaria tenuis: Aspergillus, such as Aspergillus niger; Chaetomium, such as Chaetomium globosum; Coniophora, such as Coniophora puetana; Lentinus, such as Lentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporus, such as Polyporus versicolor, Aureobasidium, such as Aureobasidium pullulans; Sclerophoma, such as Sclerophoma pityophila Trichoderma, such as Trichoderma viride Qphiostoma spp., Ceratocystis spp., Humicola spp., Peiriella spp., Trichurus spp., Coriolus spp., Gloeophyllum spp., Pleurotus spp.. Porta spp., Serpula spp. and Tyromyces spp., Cladosporium spp., Paecilomyces spp. Mucor spp., Escherichia, such as Escherichia, coli; Pseudomonas, such as Pseudomonas aeruginosa; Staphylococcus, such as Staphylococcus aureus, Candida spp. and Saccharotnyces spp., such as Saccharomyces cerevisae.
In addition, the compounds of the formula (I) also have very good antimycotic effects. They have a very broad antimycotic activity spectrum, especially against dermatophytes and yeasts, moulds and diphasic fungi (for example against Candida species, such as Candida albicans, Candida glahraia), and Epidermophyion floccosurn, Aspergillus species, such as Aspergillus niger and Aspergillus fumigatus, T ' richophyton species, such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii. The enumeration of these fungi by no means constitutes a restriction of the mycotic spectrum covered, and is merely of illustrative character. The compounds can be used also to control important fungal pathogens in fish and Crustacea farming, e.g. saprolegnia diclina in trouts, saprolegnia parasitica in crayfish.
The compounds of the formula (I) can therefore be used both in medical and in non-medical applications. The compounds of the formula (I) can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. Application is accomplished in a customary manner, for example by watering, spraying, atomizing, broadcasting, dusting, foaming, spreading-on and the like. It is also possible to deploy the active ingredients by the ultra-low volume method or to inject the active ingredient preparation/the active ingredient itself into the soil. It is also possible to treat the seed of the plants.
It is possible to treat all plants and their parts in accordance with the invention, preferably with wild plant species and plant cultivars, or those obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and also parts thereof. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The terms "parts" or "parts of plants" or "plant parts" have been explained above. More preferably, plants of the plant cultivars which are commercially available or are in use are treated in accordance with the invention. Plant cultivars are understood to mean plants which have new properties ("traits") and have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be cultivars, varieties, bio- or genotypes.
The method of treatment according to the invention can be used in the treatment of genetically modified organisms (GMQs), e.g. plants or seeds. Genetically modified plants (or transgenic plants) are plants of which a heterologous gene has been stably integrated into genome. The expression "heterologous gene" essentially means a gene which is provided or assembled outside the plant and when introduced in the nuclear, chloroplastic or mitochondrial genome gives the transformed plant new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by downregulating or silencing other gene(s) which are present in the plant (using for example, antisense technology, cosuppression technology, RNA interference - RNAi - technology or microRNA - miRNA - technology). A heterologous gene that is located in the genome is also called a transgene. A transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.
Plants and plant cultivars which are preferably to be treated according to the invention include all plants which have genetic material which impart particularly advantageous, useful traits to these plants (whether obtained by breeding and/or biotechnological means). Plants and plant cultivars which are also preferably to be treated according to the invention are resistant against one or more biotic stresses, i.e. said plants show a better defense against animal and microbial pests, such as against nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and/or viroids. Plants and plant cultivars which may also be treated according to the invention are those plants which are resistan to one or more abiotic stresses. Abiotic stress conditions may include, for example, drought, cold temperature exposure, heat exposure, osmotic stress, flooding, increased soil salinity, increased mineral exposure, ozone exposure, high light exposure, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients, shade avoidance. Plants and plant cultivars which may also be treated according to the invention, are those plants characterized by enhanced yield characteristics. Increased yield in said plants can be the result of, for example, improved plant physiology, growth and development, such as water use efficiency, water retention efficiency, improved nitrogen use, enhanced carbon assimilation, improved photosynthesis, increased germination efficiency and accelerated maturation. Yield can furthermore be affected by improved plant architecture (under stress and non- stress conditions), including but not limited to, early flowering, flowering control for hybrid seed production, seedling vigor, plant size, internode number and distance, root growth, seed size, fruit size, pod size, pod or ear number, seed number per pod or ear, seed mass, enhanced seed filling, reduced seed dispersal, reduced pod dehiscence and lodging resistance. Further yield traits include seed composition, such as carbohydrate content and composition for example cotton or starch, protein content, oil content and composition, nutritional value, reduction in anti -nutritional compounds, improved processabiiity and better storage stability. Plants that may be treated according to the invention are hybrid plants that already express the characteristic of heterosis or hybrid vigor which results in generally higher yield, vigor, health and resistance towards biotic and abiotic stresses).
Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may be treated according to the invention are herbicide-tolerant plants, i.e. plants made tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation, or by selection of plants containing a mutation imparting such herbicide tolerance. Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are insect-resistant transgenic plants, i.e. plants made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such insect resistance.
Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are tolerant to abiotic stresses. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such stress resistance.
Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention show altered quantity, quality and/or storage- stability of the harvested product and/or altered properties of specific ingredients of the harvested product.
Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as cotton plants, with altered fiber characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered fiber characteristics.
Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as oilseed rape or related Brassica plants, with altered oil profile characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered oil profile characteristics.
Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as oilseed rape or related Brassica plants, with altered seed shattering characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered seed shattering characteristics and include plants such as oilseed rape plants with delayed or reduced seed shattering. Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as tobacco plants, with altered post-translational protein modification patterns.
Compounds of the present invention as defined by formula (I) or in table 1 may be prepared, in known manner, in a variety of ways as described in Schemes 1-4.
Figure imgf000078_0001
(I)
PREPARATION OF 4~ SUBSTITUTED -1, 2, 3-THIADIAZOLE-5-CARBOXYLIC ACID CHLORIDE
R
Figure imgf000078_0002
A compound of formula (5) is prepared as per the procedure reported in Med. Chem. Research, 22, 1747-1755 (2013). A compound of formula (1) is reacted with compound of general formula (2) to get a compound of formula (3). The compound (3) is cyelized to get a 1 ,2,3-thiadiazole derivative of formula (4). The derivative (4) is hydrolysed to get a compound of formula (5). The compound (5) is halogenated to get the acid chloride of formula (6),
PREPARATION OF 4~ SUBSTITUTED -1, 2, 3 - THIADI A ZOLE-5 - C ARB OX A IDES
Compounds of formula (4), (5) and (6) can be used to prepare L 2, 3 -Thiadiazoie compounds of the formula (8) by any of the processes illustrated below.
Method 1 : (Amide formation from Acid chlor
Figure imgf000079_0001
The acid halide of formula (6) is reacted with an amine of the general formula (7) to get the compound of formula (8).
Method 2: (Amide formation from Acid)
Figure imgf000079_0002
The acid of formula (5) is reacted with an amine of the general formula (7) using in the presence of suitable condensing agent to get the compound of formula (8).
Method 3: (Amide formation from ester)
Figure imgf000079_0003
The acid of formula (4) is reacted with an amine of the general formula (7) using in the presence of suitable condensing agent to get the compound of formula (8).
PREPARATION OF 4- SUBSTITUTED -1, 2, 3-THIADIAZOLE-5-THIO
Figure imgf000080_0001
The amide of formula (8) is treated with suitable thionating agent to give thioamide of formula (9).
Figure imgf000080_0002
N-substituted formula of (7) can be prepared by known processes such as reductive animation of aldehydes or ketones (Bioorganics and Medicinal Chemistry Letters 16 (2006) 2013-2016 or reduction of imines (Tetrahedron, 61 (49), 11521-1 1764, 2005), or nucleophilc substitution of a halogen (journal of Medicinal chemistry 45 (18), 3878-3890, 2002)
The present invention is further illustrated in the following non-limiting examples. Structures of novel compounds were confirmed by NMR and/or other appropriate analysis as given below.
EXAMPLE 1
Preparation of 4-(difluoromethyl)-N-(3-(trifluoromethoxy)phenyl)-l, 2, 3-thiadiazole~5~ carboxamide (Compound 69)
Step A: Benzyl (Z)-2-(4-ethoxy-l,l-difluoro-4-oxobutan-2-ylidene)hydrazine-l-carboxylate
To a suspension of ethyl 4,4-difluoro-3-oxobutanoate (25 gm, 150 mmol) in etlianol, was added benzyl hydrazinecarboxylate (30.0 g, 181 mmol) and the reaction mixture was heated to reflux (90°C) for 16 hours. After the completion of the reaction, the reaction mixture was concentrated under reduced pressure to give a desired product benzyl (Z)-2-(4-ethoxy-l,l-difiuoro-4- oxobutan-2-ylidene)hydrazine-l-carboxylate (47 g, 150 mmol) as a gum. LCMS (m-H)" 312.95 Step B: Ethyl 4-(difluoromethyl)-l, 2, 3-thiadiazole-5-carboxylate
To an ice cold solution of benzyl (Z)-2-(4-ethoxy-l ,l-difluoro-4-oxobutan-2-lidene)hydrazine-l- carbox late (47 g, 150 mmol) in chloroform was added thionyl chloride (142 ml, 1944mmol) dropwise. Reaction mixture stirred at 60°C for 4 hours. The reaction mixture was concentrated under reduced pressure, diluted with ice cold water and neutralized with sodium bicarbonate solution to neutral pH. The aqueous layer was extracted with ethyl acetate three times (3x800 ml). The organic phase was dried over anhydrous sodium sulphate and concentrated under reduced pressure. The resulting residue was then purified by column chromatography on silica gel using Hexane:Ethyl acetate as eluent to give desired ethyl 4-(difluoromethyl)-l , 2, 3- thiadiazole-5-carboxylate (25 g, 120 mmol) as a yellow liquid. 1H-NMR (400 MHz, DMSO-d6) 5 7.60 (ί, J - 52,7 Hz, 1H), 4.40 (q, J = 7.1 Hz, 21 ! }. 1 ,32 (t, J = 7.1 Hz, 3H)
Step C; 4-(difluoromethyl)-l, 2, 3-thiadiazoIe-5-carboxyIic acid
To a solution of ethyl 4-(difluoromethyl)-l, 2, 3-thiadiazole-5-carboxylate (20 g, 96 mmol) in THF: Water (4: 1), Lithium hydroxide monohydrate (12.09 g, 288 mmol) was added and the reaction mixture was stirred at 30°C for 4 hours. After the completion of the reaction, the reaction mixture was neutralized with IN hydrochloric acid and then extracted with 20% IPA in CHCI3 (3x600 ml). The organic phase was dried over anhydrous Na2S04 and concentrated under reduced pressure, to give the desired 4-(difluoromethyl)-l, 2, 3-thiadiazole-5-carboxylic acid (15 g, 83 mmol) as a solid. LCMS (m-H)" : 179.20; 1H-NMR (400 MHz, DMSO-d6) δ 7.60 (t, J = 52.9 Hz, 1H).
Step D: Preparation of 4-(difluoromethyl)-N-(3-(trifluoromethoxy)phenyl)-l, 2, 3- thiadiazole-5-carboxamide
To a solution of 4-(difluorometliyl)-l,2,3-thiadiazole-5-carboxylic acid (400 mg, 2.221 mmol) in DCM was added DIPEA (1.16 ml, 6.64 mmol), 1-Propanephosphonic acid cyclic anhydride (1 ml, 3.36mmol) and 3-(trifluoromemoxy)aniline (0.31 ml, 2.221 mmol) and the reaction mixture was stirred at 30°C for 16 hours. The reaction mixture was extracted with dichloromethane (2x20 ml). The organic phase was dried over anhydrous Na2S04 and evaporated under reduced pressure. The resulting residue was then purified by column chromatography on silica gel using Hexane:Ethyl acetate as eluent to give the desired 4-(difluoromethyl)-N-(3- (trifluoromethoxy)phenyl)-l, 2, 3-thiadiazole-5-carboxamide (350 mg, 1.032 mmol) as a gum. LCMS (m-H)" 337.80, 1 H-NMR (400 MHz, DMSO-d6) δ 1 1 .25 (s, 1H), 7.80 (s, l H), 7.49-7.76 (m, 3H), 7.18 (dt, J = 8.2, 1.1 Hz, l i t ).
Preparation of N-(4-(pentafluoro^-sulfanyl)phenyl)-4^trifluoromethyl)-l, 2, 3- thiadiazole-5-carboxamide (Compound 24)
Step-A; Ethyl (Z)-2~(4-ethoxy~l,i,l-trifluoro-4~oxobistan~2~ylidene)hydrazine~l- carboxylate
To a solution of ethyl 4,4,4-trifluoro-3-oxobutanoate (5.0 gm, 27.2 mmol) in ethanol was added ethyl hydrazinecarboxylate (2.83g, 27.2 mmol) and the reaction mixture was heated at 70°C for 48 hours. Solvent was evaporated under reduced pressure to get a residue. The residue was purified by column chromatography on silica gel using Hexane:Ethyl acetate as eluent to give the desired ethyl (Z)-2-(4-ethoxy- 1,1,1 -trifluoro-4-oxobutan-2-ylidene)hydrazine- 1 -carboxyiate (2.5g, 9.25 mmol) as a solid. LCMS (m-H)" 268.95
Step-B: Ethyl 4-(trifluoromethyl)-l, 2, 3-thiadiazoIe-5~carfooxyIate
To a solution of ethyl (Z)-2-(4-ethoxy-l,l ,l-trifluoro-4-oxobutan-2-ylidene)hydrazine-l- carboxylate (2.5g, 9.25 mmol) in chloroform (25 ml), thionyl chloride (13.7 mi, 185 mmol) was added drop-wise at room temperature and reaction mass was stirred at 70°C for 48 hours. The reaction mixture was concentrated under reduced pressure, diluted with ice cold water and neutralized with sodium bicarbonate solution to neutral pH. The aqueous layer was extracted with ethyl acetate three times. (3x 100ml). The orgamc phase was dried over anhydrous sodium sulphate and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel using Hexane:Ethyl acetate as eluent to give the desired ethyl 4- (trifluoromethyl)-l, 2, 3-thiadiazole-5-carboxylate (0.5g, 2.211 mmol) as a yellow liquid. 1H- NMR (400 MHz, DMSO-d6) δ 4.41 (q, 2H), 1.31 (t, J = 7.0 Hz, 3H)
Step-C: Preparation of N-(4-(pentafluoro- 6-sulfanyl)phenyl)-4-(trifluoromethyl)-l,2,3- thiadiazole-5-carboxamide
A stirred solution of ethyl 4-(trifluoromethyl)-l,2,3-thiadiazole-5-carboxylate (300 mg, 1.32 mmol) and (p-aminophenyl) sulfurpentafluoride (291 mg, 1.32 mmol) in toluene was added trimethylaluminum (2.0 M in Toluene) solution (2.65 ml, 5.31 mmol) drop-wise at 25°C and the reaction mixture was stirred for 12 hours. Saturated ammonium chloride solution (20 niL) was added to the reaction mixture, diluted with water and extracted with ethyl acetate (2x25 ml). Organic layer was separated, dried over sodium sulphate and evaporated to get crude which was purified by column chromatography on silica gel using Hexane:Ethyl. acetate as eluent to give the desired N-(4-(pentafluoro-X6-sulf anyl)phenyl)-4-(trifluoromethyl)- 1 , 2, 3-fhiadiazole-5- carboxamide (350 mg, 0.877 mmol) as a solid. LCMS (m-H)" 397.85; 1H-NMR (400 MHz, DMSQ-d6) δ 11.48 (s, 1H), 7.95 (dd, J = 7.3, 2.1 Hz, 2H), 7.82 (d, / = 9.0 Hz, 2H) EXAMPLE 3;
Preparation of 4-(dmuoromethyl)-N-(4-(pentafluoro^-sulfanyl)phenyl)-l, 2, 3- thiadiazoIe-5-carboxamide (Compound 3)
To a solution of 4-(difluoromethyl)-l ,2,3-thiadiazole-5-carboxylic acid (296 mg, 1.643 mmol) and HATU (781 mg, 2.053 mmol) in Ν,Ν-dimethylformamide was added (p-aminophenyl) sulfurpentafluoride (300mg, 1.369 mmol) and DIPEA (0.84 ml, 4.8 mmol) and the reaction mixture was stirred at room temperature for 5 hours. The reaction mixture was diluted with water
(50ml) and extracted with ethyl acetate (2x50ml). Organic phase was washed with brine solution, dried over sodium sulphate and evaporated to get crude which was purified by column chromatography on silica gel using HexanerEthyl acetate as eluent to give the desired 4- (difluoromethyl)-N-(4-(penta†Iuoro^ (0.26 g, 0.682 mmol) product. LCMS (m-H)" 379.8, 1H-NMR (400 MHz, DMSO-d6) δ 11.39 (s, 1H), 7.97-7.94 (m,2H), 7.88 (s, 1H), 7.86 7 (s, 1 H), 7.76-7.50 (t, J= 53.2, 1 H).
EXAMPLE 4;
Preparation of 4-(difluoromethyl)-N-(4-(pentafluoro- 6-sulfaiiyl)phenyl)-l, 2, 3- thiadiazoIe~5-carbothioamide (Compound 4)
To a solution of 4-(difluoromethyl)-N-(4-(pentafluoro- 6-sulfanyl)p enyl)- 1 , 2, 3-thiadiazol.e-5- carboxamide (0.2 g, 0.525 mmol) in toluene was added lawesson's reagent (0.64g, 1.58 mmol). The reaction mixture was heated at 1 10 °C for 24 hours. The reaction mixture was cooled, concentrated under vacuum to get the crude product. The crude product was purified by preparative HPLC to afford 4-(difluoromethyl.)-N-(4-(pentafluoro- 6-sulfanyl)phenyl)-l, 2, 3- thiadiaz.ole-5-carbothioamide (0.136 g, 0.342 mmol) as a product. LCMS (m-H)" 395.85, 1H- NMR (400 MHz, DMSO-d6) δ 12.93 (s, I I I ), 8.07 (br, 2H), 8.02 (d, J = 8.7 Hz, 2H), 7.63 (t, J 52.7 Hz, 1H).
EXAMPLE 5;
Preparation of N-(2-chloro-4-(pentafluoro- 6-sulfanyl)phenyl)-4-(difluoromethyl)-l, 2, 3- thiadiazole-5-carboxamide (Compound 5)
Step A: 4-(difluoromethyl)-N-(4-(pentafluoro- 6-sulfanyl)phenyl)-l, 2, 3-tfaiadiazoIe-§- carboxamide
To a solution of 4-(difluoromethyl)-l, 2, 3-thiadiazole-5-carboxylic acid (296 mg, 1.643 mmol) and HATU (780 mg, 2.05 mmol) in N,N-dimemylformamide was added (p-aminophenyl) sulfurpentafluoride (300 mg, 1.369 mmol) and DIPEA (0.84 ml, 4.8 mmol) and the reaction mixture was stirred at room temperature for 5 hours. The reaction mixture was diluted with water (50 ml) and extracted with EtOAc (2x50 ml). Organic phase was washed with brine solution, dried over sodium sulphate and evaporated to get crude which was purified by column chromatography on silica gel using HexanerEthyl acetate as eluent to give the desired 4- (difluoromemyl)-N-(4-( entafluoro- 6-sulfanyl)phenyl)-l,2,3-thiadiazole-5-carboxamide (0.26 g, 0.682 mmol, ) product. LCMS (m-H)' 379.8, 1H-NMR (400 MHz, DMSO-d6) δ 1 1.39 (s, 1H), 7.97-7.94 (m,2H), 7.88 (s, 1H), 7.86 7 (s, 1H), 7.76-7.50 (t, J = 53.2 Hz, 1H). Step B: N-(2-chloro-4-(pentafluoro- 6-sulfanyl)phenyl)-4-(difluoromethyl)-l, 2, 3- thiadiazole-5-carboxamide
To a solution of 4-(difluoromethyl)-N-(4-(pentafluoro- 6-sulfanyl)p enyl)- 1 , 2, 3-ihiadiazole-5- carboxamide (0.3 g, 0.787 mmol) in methanol and water, was added sodium periodate (0.841 g, 3.93 mmol) and hydrochloric acid (7.5 mi, 86 mmol) at room temperature and the reaction mixture was stirred for 12 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (2x25 ml). Organic layer phase was washed with brine solution, dried over sodium sulphate and evaporated to get crude product which was purified by column chromatography on silica gel using HexanerEthyl acetate as eluent to give the desired N-(2-chloro-4-(pentafluoro- 6- sulfanyl)phenyl)-4-(difluoromethyl)- l, 2, 3-thiadiazole-5-carboxamide (0.125 g, 0.301 mmol). LCMS (m-H)" 413.75, 1H-NMR (400 MHz, DMSO-d6) δ 11.12 (s, 1H), 8.20 (d, J = 2.3 Hz, 1H), 8.06 (d, J = 9.2 Hz, 1 H), 8.02 (dd, J = 9.1, 2.4 Hz, 1H), 7.63 (t, J = 52.9 Hz, 1 H).
EXAMPLE 6:
Preparation of N-(2-Bromo-4-(pentafluoro- 6-sulfanyl)pheiiyl)-4-(difluoromethyl)-l, 2, 3- thiadiazole-5-carboxamide (Compound 14)
To a solution of 4-(difluoromethyl)-N-(4-(pentafluoro- 6-sulfanyl)phenyl)-l, 2, 3-thiadiazole-5- carboxamide (0.15 g, 0.393 mmol) in methanol and water, was added sodium periodate (0.38 g, 1.77 mmol), sulfuric acid (0.5 ml, 9.38 mmol) and hvdrobromic acid (1.0 ml, 18.42 mmol) at 0 °C and the reaction mixture was stirred at rt for 12 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (2x25mi). Organic phase was washed with brine solution, dried over sodium sulphate and evaporated to get crude product which was purified by column chromatography on silica gel using Hexane:Ethyl acetate as eluent to give the desired N-(2- bromo-4-(pentafluoro- 6-sulfanyl)phenyl)-4-(difluoromethyl)- 1 , 2, 3-thiadiazole-5-carboxamide (0.1 115 g, 0.250 mmol). LCMS (m-H)" 457.8, 1H-NMR (400 MHz, DMSO-d6) δ 11.11 (s, lH), 8.31 (d, J - 2.4 Hz, 1H), 8.07 (dd, J - 9.0, 2.4 Hz, 1H), 7.96 (d, J = 8.9 Ηζ,ΙΗ), 7.63 (t, J = 52.9 Hz, H i ).
EXAMPLE 1%
Preparation of N-(3,5-Dichloro-4-phenyl)-4-(difluoromethyl)-l, 2, 3-thiadiazoLe-5- carboxamide (Compound 145)
To a solution of 4-(difluoromethyl)-l, 2, 3-thiadiazole-5-carboxylic acid (500 mg, 2.78 mmol) in toluene (20 ml) at 0°C, was added thionyl chloride (2.013 ml, 27.8 mmol) and heated to 100 °C for 3 hours. Solvent was distilled off completely and then dissolved in dry dichloroniethane and kept under nitrogen. To a solution of 3,5-dichloroaniline (450 mg, 2.78 mmol) in DCM (10.00 ml) at 0°C was added N-ethyl-N-isopropylpropan-2-amine (1.451 ml, 8.33 mmol), stirred for 5 min then added above prepared acid chloride solution dropwise over a period of 10 min then stirred at room temperature for 3 hours. The reaction mixture was d luted with water and extracted with DCM (3x50 ml). Organic phase was dried using sodium sulfate and concentrated to get the crude product, which was purified by columan chromoto graph y on silica gel using5()% ethyl acetate and hexane to get N-(3,5-dichlorophenyl)-4-(difluoromethyl)- l, 2, 3~thiadiazole-5- carboxamide (380 mg, 1.172 mmol). LCMS (m-H)" 322.0, 1H-NMR (400 MHz, DMSO-d6) δ 11.28 (s, I I I ). 7.49-7.75 (m. M l ). 7.44 (t, J = 1.8 Hz, H i }. EXAMPLE 8:
Preparation of N-(4-bromo-2-(trifluoromethyl)phenyl)-4-(difluoromethyl)-N-methyl-l, 2, 3- thiadiazole-5-carboxamide (Compound 107)
Step A: N-(4-bromo-2-(trifluoromethyl)phenyl)-4-(difluoromethyl)-l, 2, 3-thiadiazole-5- carboxamide
To a stirred solution of 4-(difluoromethyl)-l, 2, 3-thiadiazole-5-carbonyl chloride (0.54 g, 2.72 mmol) and 4-bromo-2-tri.fluoromethyl aniline (0.5 g, 2.083 mmol) in dichloromethane was added DIPEA (1.1 ml. 6.3 mmol). The reaction mixture was stirred at room temperature for 24 hours. The reaction mixture extracted with ethyl acetate (2 x 50ml). Organic phase was washed with water, dried over sodium sulphate and evaporated to get crude product which was purified by column chromatography on silica gel using Hexane:Ethyl acetate as eluent to give the desired N-(4-bromo-2-(trifluoiOmethyl)phenyl)-4-(difluoiOmethyl)- l, 2, 3-thiadiazoIe-5-carboxamide (0.395 mg, 0.982 mmol). LCMS (m-H)" 401.8, 1H-NMR (400 MHz, DMSO-d6) δ 11.03 (s, 1H), 8.06-7.98 (m, 2H), 7.69 (d, J = 9.2 Hz, 1H), 7.58 (t, J = 53.0 Hz, 1H).
Step B: N-(4-bromo-2-(trifluoromethyl)phenyl)-4-(difluoromethyl)-N-methyl-l,2,3- thiadiazole-5-carboxamide
To a Solution of N-(4-bromo-2-( fluoromethyl)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carboxamide (0.170 g, 0.423 mmol) in DMF was cooled to 0°C and added sodium hydride (25.4 mg, 0.634 mmol) and stirred for 15 mini. Methyl iodide (0.08 ml, 1.28 mmol) was added and stirred at 40°C for 16 hours. Reaction mixture was diluted with water and extracted with ethyl acetate (2x10ml). Organic phase was washed with water, dried over sodium sulfate and concentrated to get crude which was purified by column chromatography on silica gel using Hexane:Ethyl acetate as eluent to give the desired N-(4-bromo-2-(trifluoromethyl)phenyl)-4- (difluoromethyl)-N-methyl-l,2,3-thiadiazole-5-carboxamide (110 mg, 0.264 mmol). GCMS (M) 415, 1H-NMR (400 MHz, DMSO-d6) δ 8,09-8.15 (m, 2H), 7.85 (d, J = 8.4 Hz, 1H), 7.42-7.68 (m, 1H), 3.34 (s, 3H). EXAMPLE 9
Preparation of N-(2-Chloro-4-(trifluoromethyl)sulfinyl)phenyl)-4-(difluoromethyl)-l,2,3- thiadiazole-5-carboxamide (Compound 48)
Step A: 4-(difluoromethyl)-N-(3-((trifluoromethyl)thio)phenyl)-l,2,3-thiadiazole-5- carboxamide
To a solution of 4-(trifluoromethyl)thioaniline (0.72 ml, 5.03 mmol) in dichloromethane was added DIPEA (4.40 ml, 25.2 mmol) and 4-(difluoromethyl)-l,2,3-thiadiazole-5-carbonyl chlroride (1 g, 5.04 mmol) in DCM dropwise. Reaction mixture was stirred at room temperature for 6 hours. Reaction mixture was diluted with water and extracted with DCM (2 x 20 ml). Organic layer was separated, dried over sodium sulfate, concentrated under reduced pressure to give crude, which was purified by column chromatography to give 4-(difluoromethyl)-N-(4- ((trifliioromethyl)thio)phenyl)-l,2,3-thiadiazole-5-carboxamide (1 g, 2.81 mmol). LCMS (m-H)" 353.85, 1H-NMR (400 MHz, DMSO-d6) δ 1 1.28 (s, 1H), 7.50-7.82 (m, 5H).
Step B: N-(2-Chloro-4(trifluoromethyl)sulfinyl)phenyl)-4-(difluoromethyl)-l,2,3- thiadiazole-5-carboxamide
To a stirred solution of 4-(difluoromemyl)-N-(4-((trMuoromemyl)mio)phenyl)- 1,2,3 -thiadiazole- 5-carboxamide (200 mg, 0.563 mmol) in methanohwater (2: 1) was added sodium periodate (602 mg, 2.81 mmol) and hydrochloric acid ( 1.881 ml, 61.9 mmol) dropwise at room temperature. The reaction mixture was heated at 60°C for 2 hours. Reaction mixture was neutralized with saturated sodium bicarbonate solution and extracted with ethyl acetate. Organic phase was dried over sodium sulfate and concentrated to get the crude product which was purified by column chromatography to give to get N-(2-Chloro-4-(trifluoromethyl)sulfinyl)phenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carboxamide (160 mg, 0.394 mmol). LCMS (m-H)" 403.8, 1H-NMR (400 MHz, DMSO-d6) 6 1 1.13 (s, 1 H), 8, 15 (d, J = 8.6 Hz, 1H), 8.09 (d, .1 = 1.7 Hz, 1H), 7.95 (dd, J = 8.6, 1.5 Hz, 1H), 7.64 (i, J = 52.9 Hz, 1H).
EXAMPLE 10
Preparation of N 2-BroBio~4(triilaoromethyl)thio)pheiiyI)-4-(diflaoromethyl)-i,2,3- thiadiazole-5-carboxamide (Compound 44)
Step A: 2-Bromo-4-(trifluoromethyl)aiuline
To a solution of 4-(trifluoromethyl)aniline (200 mg, 1.035 mmol) in acetonitrile was added N- bromosuccinamide (203 mg, 1.139 mmol). Reaction mixture was stirred at room temperature for
16 hours. Reaction mixture was filtered and concentrated. The resulting crude product was purified by column chromatography to give 2-Bromo-(4-trifluoromethyl)thio)aniline (200 mg, 0.735 mmol). 1H-NMR (400 MHz, DMSO-d6) δ 7.63 (d, J = 2.0 Hz, I I I). 7.35 (dd, J = 8.5, 2.1 Hz, 1H), 6.83-6.85 (m, 1H), 6.05 (s, 2H)
Step B: N-(2-Bromo-4(trifluoromethyl)thio)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carboxamide
To a stirred solution of ethyl 4-(difluoroniethyl)-l.,2,3-thiadiazole-5-carboxalate (400 mg, 1.921 mmol) in Toluene was added 2-Bromo-(4-trifluoiOmethyl)thio)aniline (523 mg, 1.921 mmol) was added and trimethyl aluminium (3.84 ml, 7.69 mmol). Reaction mixture was stirred at room temperature for 16 hours. Reaction mixture was treated with saturated ammonium chloride solution, extracted with ethyl acetate (2 x 30 ml). Organic phase was dried over sodium sulfate and concentrated. The resulting crude product was purified by column chromatography to give N-(2-Bromo~4(trifluoromemyl)to
(85 mg, 0.196 mmol). LCMS (m-H)" 431.75, 1 H-NMR (400 MHz, DMSO-d6) δ 11.03 (s, 1H), 8.11 (d, J = 1.7 Hz, 1H), 7.82-7.88 (m, 2H), 7.64 (t, J = 52.9 Hz, 1H). EXAMPLE 11
Preparation of N-(3-(N-cyanopropan-2-ylsulfonimidoyl)phenyl)-4-(difluoromethyl)-l,2,3- thiadiazole-5-carboxamide. (Compound 234)
Step A: 3-(isopropylthio)aniline.
To a stirred solution of aminobenzenethiol (1 g, 7.99 mmol) and 2-bromopropane (1.179 g, 9.59 mmol) in DMF, was added potassium carbonate (1.656 g, 11.98 mmol). Reaction mixture was stirred at room temperature for 3 hours. Reaction mixture was diluted with water (50 ml) and extracted with ethyl acetate (2 x 50 ml ). Organic phase was dried over sodium sulfate and concentrated. The resulting crude product was purified by column chromatography to give 3-
(isopropylthio) aniline (1.12 g, 6.70 mmol). LCMS (m+H)+: 168.
Step B: 4-(difluoromethyl)-N-(3-(isopropylthio)phenyl)-l,2,3-thiadiazole-5-carboxamide
To a stirred solution of 3-(isopropylthio)aniline (1 g, 5.98 mmol) in DCM was added DIPEA
(8.35 ml 47.8 mmol) at 0°C. After 5 minutes 4-(difluoromethyl)-l , 2, 3-thiadiazole-5-carbonyl chloride (1.54 g, 7.75 mmol) was added to the reaction mixture at 0°C. Reaction mixture was stirred for 18 hours at room temperature. Reaction mixture was treated with water (50 ml) and extracted with DCM (2 x 50 mi ). Organic phase was dried over sodium sulfate and concentrated. The resulting crude product was purified by column chromatography to give 4-
(dffluoromethyl)-N-(3 -(isopropylthio)phenyl)- 1 , 2, 3-miadiazole-5-carboxamide (1.7 g, 5.16 mmol). LCMS (m-H)" 327, 1H-NMR (400 MHz, DMSO-d6) δ 1 1.02 (s, 1 1 1), 7.73 (t J = 1.8 Hz,
1H), 7.62 (t, J = 52.9 Hz, 1H), 7.51-7.46 (m, 1 H), 7.35 (t, J = 8.0 Hz, 1 H), 7.17 (dt, J = 7.8, 1.4 Hz, 1H), 3.47 (septet, J = 6.6 Hz, 1H), 1.25 (d, J = 6.9 Hz, 6H). Step C: (E)-N-(3-(N-cyano-S-isopropylsulfinimidoyl)phenyl)-4-(difluoroinethyl)-l, 2, 3- thiadiazole-5-carboxamide. (Compound 233)
To a stirred solution of 4-(difluoromethyl.)-N-(3-(isopropylthio)phenyl)-l,2,3-thiadiazole-5- carboxamide (0.6 g, 1.822 mmol) in acetonitrile, were addeed iodobenzene diacetate (0.880 g, 2.73 mmol) and cyanamide (0.15 g, 3.57 mmol) successively at room temperature. Reaction mixture was stirred for 16 hours at room temperature. Reaction mixture was diluted with water (50 ml.) and extracted with ethyl acetate (2 x 50 ml ). Organic phase was dried over sodium sulfate and concentrated. The resulting crude product was purified by column chromatography to give (E)-N-(3-(N-cyano-S-isopropylsulfinimidoyl)phenyl)-4-(difluoromethyl)- 1 , 2, 3- thiadiazole-5-carboxamide (503 mg, 1.362 mmol). LCMS (m-H)" 367.9, IH-NMR (400 MHz, DMSQ-d6) δ 11.40 (s, III), 8.18 (s, IH), 7.93 (d, J = 8.2 Hz, H I ). 7.70 (L J = 7,8 Hz, i l l ). 7.64 (t, J = 52.7 Hz, 1 H), 7.63 (d, J = 6.9 Hz, IH), 3.59 (septet, J = 6.6 Hz, 1 H), 1 .26 (d, J = 6.9 Hz, 3H), 1.12 (d, J = 6.4 Hz, 3H).
Step D: N-(3-(N-cyanopropan-2-ylsulfonimidoyl)phenyl)-4-(difluoromethyl)-l, 2, 3- thiadiazole-5-carboxamide.
To a stirred solution of (E)-N-(3-(N-cyano-S-isopropylsulfinimidoyl)phenyl)-4-(difluoromethyl)- 1, 2, 3-thiadiazole-5-carboxamide (0.4 g, 1.083 mmol) in DCM:Acetonitrile:Water (1: 1: 1) were added Sodium periodate (0.46 g, 2.16 mmol) and Ruthenium (III) chloride(0.01g, 0.05 mmol) successively at cooled condition. Reaction mixture was stirred for 16 hours at room temperature. Reaction mixture was diluted with water (50 ml) and extracted with ethyl acetate (2 x 25 ml ). Organic phase was dried over sodium sulfate and concentrated. The resulting crude product was purified by column chromatography to give N-(3-(N-cyanopropan-2-ylsulfonimidoyl)phenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carboxamide (0.218g, 0.55 mmol). LCMS (m-H)" 383.9, IH-NMR (400 MHz, DMSO-d6) δ 11.48 (s, IH), 8.34 (t, J = 1.8 Hz, IH), 8.15-8.04 (m, IH), 7.83 (t, J = 7.8 Hz, IH), 7.81-7.75 (m, IH), 7.64 (t, J = 52.7 Hz, IH), 3.98 (septet, J = 6.6 Hz, IH), 1.33 (d, J = 6.9 Hz, 3H), 1.21 (d, J = 6.9 Hz, 3H).
The following table illustrate in a non-limiting manner examples of compounds according to the invention. In the following examples, M+l (or M-l) means the molecular ion peak, plus or minus 1 a.m.u. (atomic mass unit) respectively, as observed in mass spectroscopy lH-NMR data of selected examples are written in form ofΉ-NMR-peak lists. To each signal peak are listed the 6- value in ppm and the no of proton in round brackets.
For calibrating chemical shift for lH spectra, we use tetrameihylsilane and/or the chemical shift of the solvent used, especially in the case of spectra measured in DMSO. Therefore in NMR peak lists, tetramethylsilane peak can occur but not necessarily. Table-l provides compounds of general formula (I)
Figure imgf000089_0001
14 N-(2-bromo-4-(pentafluoro-16- 1H-NMR (400 MHz, DMSO-i¾) δ 11.11 (s, 1 H), 8.31 sulfaneyl)phenyl)-4- (d, ,/ = 2.4 Hz, IH), 8.07 (dd, 7 = 9.0, 2.4 Hz, I H), 7.96 (difluoromethyl)- 1 ,2,3-thiadiazoIe-5- (d, J = 8.9 Ηζ,ΙΗ), 7.63 (t, J = 52.9 Hz, IH)
carboxamide
15 N-(2-bromo-4-(pentafluoro-16- 'H-NMR (400 MHz, CDC13) δ 9.60 (s, IH), 8.53 (d, / sulfaneyl)phenyl)-4- = 7.5 Hz, IH), 8.22-7.98 on. IH), 7.98-7.72 (rn, IH), (difluoromethyl)- 1 ,2,3-thiadiazoIe-5- 7.45 (I . ./ - 53.6 11/. IH)
carbothioamide
16 4- (drfluoromethyl)-N-(4- 'H-NMR (400 MHz, DMSO-i¾s) δ 11.29 (s, IH), 8.34 (methylthio)-3-(pentafluoro-16- (d, ,/ = 2.1 Hz, IH), 7.85 (dd, ,/ = 8.7, 2.0 Hz, IH), sulf aneyl)phenyl)- 1 ,2,3-thiadiazole- 7.50-7.76 (m, 2H), 2.58 (s, 3H)
5- carboxamide
17 4- (drfluoromethyl)-N-(4- 'H-NMR (400 MHz, DMSO-i¾ δ 12.68 (s, IH), 8.43 (methylthio)-3-(pentafluoro-16- (d, J = 2.6 Hz, IH), 8.00 (dd, J = 9.0, 2.4 Hz, IH), sulf aneyl)phenyl)- 1 ,2,3-thiadiazole- 7.46-7.75 (m, 2H), 3.96 (s, 3H)
5- carbothioamide
18 4-(difluoromet yl)-N-(4-fluoro-3- 'H-NMR (400 MHz, DMSG-i¾ δ 11.35 (s, IH), 8.34 (pentafluoro-16-sulfaneyl)phenyl)- (dd, J = 6.3, 2.5 Hz, IH), 7.91 (ddd, ,/ = 9.1, 3.9, 2.6 l,2,3-thiadiazole-5-carboxaniide Hz, IH), 7.66-7.58 (m, IH), 7.63 (i, / = 52.7 Hz, IH)
19 4-(difluoromethyl)-N-(4-fluoro-3- 'H-NMR (400 MHz,
Figure imgf000090_0001
δ 12.85 (s, IH), 8.58 (pentafluoro 46 - sulf aneyl)phenyl) - (d, J - 4.6 Hz, IH), 8.05 (d, J - 7.0 Hz, IH), 7.50-7.76 l,2,3-thiadiazole-5-carbothioamide (m, 2H)
20 4-(difluoromethyl)-N-(4-methoxy-3- 'H-NMR (400 MHz, CDC13) δ 8.19 (s, IH), 7.93 (d, / (pentafluoro 46 - sulf aneyl)phenyl) - = 2.4 Hz, IH), 7.77 (dd, J = 9.0, 2.6 Hz, IH), 7.52 (t, J 1,2,3 -thiadiazole-5 -carboxamide - 53.5 Hz, IH), 7.11 (d, J = 9.0 Hz, IH), 3.96 (s, 3H)
21 4-(difluoromethyl)-N-(4-methoxy-3- {H-NMR (400 MHz, DMSO-J5) δ 12.81 (s, IH), 8.61 (pentafluoro 46 - sulf aneyl)phenyl) - (s, IH), 8.01 (d, J - 8.1 Hz, IH), 7.49-7.75 (m, 2H), 1,2,3 -thiadiazole-5 -carbothioamide 2.61 (s, 3H)
22 N-(3-(pentafluoro-16- Ή-NMR (400 MHz, DMSO-J6) δ 11.45 (s, I H), 8.27 sul.faneyl)phenyl)-4- (t, 7 = 2.1 Hz, IH), 7.79 (d, / = 8.1 Hz, IH), 7.73 (dt,
( trifluoromethyl)- 1 ,2,3-thiadiazole-5- J = 7.2, 1.1 Hz, IH), 7.65 (t, ,/ = 8.2 Hz, IH) carboxamide
23 N-(3-(pentafluoro-16- Ή-NMR (400 MHz, DMSO-J6) δ 13.04 (s, I H), 8.55 sul.faneyl)phenyl)-4- (s, IH). 7.99 (d, ./ - 8.0 Hz, IH), 7.90 (d, ,/ = 8.3 Hz,
( trifluoromethyl)- 1 ,2,3-thiadiazole-5- lH), 7.75 (t, J - 8.1 Hz, IH)
carbothioamide
24 N-(4-(pentafluoro-16- Ή-NMR (400 MHz, DMSO-J6) δ 11.48 (s, I H), 7.95 sul.faneyl)phenyl)-4- (dd, J = 7.3, 2.1 Hz, 2H), 7.82 (d, J = 9.0 Hz, 2H)
( trifluoromethyl)- 1 ,2,3-thiadiazole-5- carboxamide
25 N-(4-(pentafluoro-16- 1H-NMR (400 M Hz, DM SO ·· /.·,) δ 13.05 is, IH), sul.faneyl)phenyl)-4- 8.03-8.08 (m, 4H)
( trifluoromethyl)- 1 ,2,3-thiadiazole-5- carbothioamide
26 N-(2-chloro-4-(pentafluoro-16- 1H-NMR (400 MHz, DMSO-J6) δ 1 1.12 (s, IH), 8.19 sulfaneyl)phenyl)-4- (d, 7 = 2.4 Hz, I H), 8.15 (d, 7 = 9.0 Hz, IH), 8.02 (dd,
( trifluoromethyl)- 1 ,2,3-thiadiazole-5- 7 = 9.0, 2.6 Hz, IH)
carboxamide
ζ..' N-(2-chloro-4-(pentafluoro-16- XH-NMR (400 MHz, CDCI3) δ 9.34 (s, IH), 8.81 (s, sulfaneyl)phenyl)-4- IH), 7.95 (d, 7 = 2.4 Hz, I H), 7.79 (dd, 7 = 8.9, 1.9
( trifluoromethyl)- 1 ,2,3-thiadiazole-5- Hz, IH) carboihioamide
4- methyl-N-(3-(pentafluoro-16- 1 H-NMR (400 MHz, CDC13) δ 8.02 (t, / = 2.1 Hz, IH), sulfaney phenyl)- 1 ,2,3-thiadiazole- 7.79 (d, / = 8.7 Hz, I H), 7.73 (s, IH), 7.62 (dd, ./ = 8.2,
5 - carboxamide 1.4 Hz, IH), 7.51 (i, J = 8.2 Hz, IH), 2.99 (s, 3H)
4- methyl-N-(3-(pentafluoro-16- 'H-NMR (400 MHz, OMSO-d6) S 12.54-12.48 sulfaneyl)phenyl)- 1 ,2,3-thiadiazole- (s.lH), 8.55 (s, IH), 8.06 (d, ./-8 Hz, I H), 7.89-7.86
5- carbothioamide (m, I H), 7.75-7.70 (m, IH), 2.77 (s, 3H)
4- methyl-N-(4-(pentafluoro-16- 1 H-NMR (400 MHz, OMSO-d6) δ 11.12 (s, IH), sulf aneyl)phenyl)- 1 ,2,3-thiadiazole- 7.95-7.91 (m,4H), 2.81 (s,3H).
5 - carboxamide
N-(2-chloro-4-(pentafluoro-16- {H-NMR (400 MHz, D SO- ) δ 10.83 (s, IH), 8.21 sulfaneyl)phenyl)-4-methyl- 1 ,2,3- (dd, J = 1 .9, 0.7 Hz, IH), 7.99 (d, J = 2.0 Hz, 2H), 2.85 thiadiazole-5-carboxamide (s, 3H)
4- isopropyl-N-(3-(pentafluoro-16- 1H-NMR (400 MHz, DMSO- ) δ 1 1.14 (s, IH), 8.33 sulfaneyl)phenyl)- 1 ,2,3-thiadiazole- (t, J = 2.1 Hz, IH), 7.90 (d, / = 8.2 Hz, I H), 7.70 (ddd,
5 - carbo amide J = 8.2, 2.2, 1.1 Hz, I H), 7.64 (t, / = 8.2 Hz, IH),
3.70-3.57 (septet, / = 6.9 Hz, IH), 1.42 (d, / = 6.9 Hz, 6H)
4- isopropyl-N-(3-(pentafluoro-16- 1H-NMR (400 MHz, CDC13) δ 9.06 (s, IH), 8.22 (s, sulfaneyl)phenyl)- 1 ,2,3-thiadiazole- IH), 7.95 (s, IH), 7.73 (d, ./ = 7.6 Hz, I H), 7.54 (d, J -
5- carbothioamide 19.3 Hz, IH), 3.59 (s, IH), 1.50 (d, J = 17.9 Hz, 6H)
4- isopropyl-N-(4-(pentafluoro-16- 1H-NMR (400 MHz, CDC13) δ 7.69-7.80 (m, 4H), 3.79 sulfaneyl)phenyl)- 1 ,2,3-thiadiazole- (m, IH), 1.54 (d, / = 6.9 Hz, 6H)
5- carboxamide
4-isopropyl-N-(4-(pentafluoro-16- 1H-NMR (400 MHz, CDC13) δ 9.03 (s, IH), 7.83-7.91 sulf aneyl)phenyl)- 1 ,2,3-thiadiazole- (m, 4H), 3.54 (s, IH), 1.51 (d, 7 = 5.7 Hz, 6H)
5 -carboihioamide
4-(difluoromethyl)-N-(3- 'H-NMR (400 MHz, DMSO- ) δ 1 1.25 (s, IH), 8.12 ((trifluoromethyl)thio)phenyl)- 1 ,2,3 - (s, I H), 7.84-7.81 (m, 2H), 7.60-7.55 (m, 2H) thiadiazole-5-carboxamide
4-(difluoromethyl)-N-(3- Ή-NMR (400 MHz, CDC13) δ 9.56 (s, IH), 8.10 (s,
((trifl u orometh yl) thiojphenyl) -1,2,3- IH), 7.88 (d, J = 7.6 Hz, I H), 7.68 (s, IH), 7.60-7.58 thiadiazole-5-carbothioamide (m, 1H),7.50 (m, I H)
4-(difluoromethyl)-N-(4- 'H-NMR (400 MHz, DMSQ-i¾) δ 11.30 (s, IH), ((trifluoromethyl)thio)phenyl)- 1 ,2,3- 7.83-7.63(m, 5H)
thiadiazole-5-carboxamide
4-(difluoromethyl)-N-(4- ' H-NMR (400 MHz, CDC33) δ 9.65 (s, I H), 7.91 (d, ./ ((trifluoromethyl)thio)phenyl)- 1 ,2,3- = 8.4 Hz, 2H), 7.76 (d, J = 8.4 Hz, 2H), 7.48 (t, J = thiadiazole-5-carbothioamide 53.7 Hz, I H)
N-(2-chloro-4- ' H-NMR (400 MHz, DMSO-^) δ 1 1 .04 (s, I H),
((trifluoromethyl)thio)phenyl)-4- 7.94-7.97 (m, 2H), 7.79 (dd, J - 8.4, 2.0 Hz, IH), 7.63
(dif uoromethyl)- l,2,3-thiadiazole-5- (t, ,7 = 52.9 Hz, I H)
carboxamide
N-(2-chloro-4- 'H-NMR (400 MHz, DMSO- ) δ 8.01 (s, I H),
((trifluoromethyl)thio)phenyl)-4- 7.53-7.81 (m, 3H)
(dif uoromethyl)- l,2,3-thiadiazole-5- carbothioamide
Figure imgf000092_0001
4-(difluoromethyl)-N-(4- 1H-NMR (400 MHz, DMSO-i¾) δ 12,57 (s, IH), 7.81 (methylthio)phenyl)- 1 ,2,3- (d, J = 8.6 Hz, 2H), 7.59 (t, / = 52.7 Hz, IH), 7.33-7.36 thiadiazole-5-carbothioaniide (m, 2H), 2.49 (s, 3H)
4-(difluoromethyl)-N-(2-fluoro-4- 1 H-NMR (400 MHz, DMSQ- ) δ 10.90 (s, IH), (methylthio)phenyl)- 1 ,2,3- 7.46-7.73 (m, 2H), 7.25 (dd, J = 11.5, 2.0 Hz, IH), thiadiazole-5-carboxamide 7.12 (dd, ,/ - 8.6, 1.7 Hz, 1H),3.86 (s, 3H); LCMS
(M-l): 317.80
4-(difluoromethyl)-N-(2-fluoro-4- Ή-NMR (400 MHz, DM O-ώ, ) δ 12.45 (s, I H), (metiiylthio)phenyl)- - 1,2,3- 7.45-7.72 (m, 2H), 7.30 (dd, J = 11.2, 2.0 Hz, I H), thiadiazole-5-carbothioamide 7.18 (dd, J - 8.4, 1.8 Hz, IH), 2.52 (s, 3H); LCMS
(M-l): 333.80
4-(difluoromethyl)-N-(2-fluoro-4- Ή-NMR (400 MHz, DMSO- ) S 11.48-10.53 (IH), (methylthio)phenyl)- 1 ,2,3- 7.85 (d, ,/ = 8.7 Hz, 2H), 7.50-7.77 (m, 3H), 2.73 (s, thiadiazole-5-carbothioamide 3H)
4-(difluoromethyl)-N-(4- 1H-NMR (400 MHz, DMSO-^) δ 11.38 (s, IH), 7.92 (methylsulfonyl)phenyl)- 1 ,2,3- (ddd, / = 20.9, 6.9, 2.1 Hz, 4H), 7.47-7.76 ( IH), thiadiazole-5-carboxamide 3.19 (s, 3H)
4-(difluoromethyl)-N-(4- 'H-NMR (400 MHz, DMSO-i¾) δ 12.89 (s, IH), 8.11 (methylsulfonyl)phenyl)- 1 ,2,3- (d, J = 7.0 Hz, 2H), 8.02 (d, J = 8.6 Hz, 2H), 7.62 (t, J = thiadiazole-5-carbothioamide 52.6 Hz, IH), 3.23 (s, 3H); LCMS (M- l ): 347.85
4-(difluoromethyl)-N-(3- 1H-NMR (400 MHz, DMSO-d6) δ 11.28 (s, I H), 8.06 (methylsulfinyl)phenyl)- 1 ,2,3- (t, J = 1.6 Hz, IH), 7.50-7.79 (m, 3H), 7.43-7.46 (m, thiadiazole-5-carboxamide IH), 2.74 (s, 3H); LCMS (M-l): 315.85
4-(difluoromethyl)-N-(3- 1H-NMR (400 MHz, DMSO- ) δ 11.36 (s, IH), 8.29 (methylsulfonyl)phenyl)- 1 ,2,3- (t, / = 1 .8 Hz, I H), 7.92-7.95 (m, I H), 7.51 -7.78 (m, thiadiazole-5-carboxamide 3H), 3.22 (s, 3H); LCMS (M-l): 331.85
4-(difluoromethyl)-N-(3- ' H-NMR (400 MHz, DMSO-i ) δ 12.87 (s, IH), 8.47 (methylsulfonyl)phenyl)- 1 ,2,3- (s, IH), 7.50-8.14 (m, 4H), 3.25 (s, 3H); LCMS (M-l): thiadiazole-5-carbothioamide 347.80
4-(difluoromethyl)-N-(2- ' H-NMR (400 MHz, DMSO-- δ 10.98 (s, I H), 7.83 (trifluoromethoxy)phenyl.)- 1 ,2,3- (d, J = 7.8 Hz, IH), 7.40-7.73 (m, 4H); LCMS (M-l ): thiadiazole-5-carboxamide 337.8
4-(difluoromethyl)-N-(2- Ή-NMR (400 MHz, DMSO- ) 12.61 (s, I H), 7.73 (trifluoromethoxy)phenyl)- 1,2,3- (t, ,/ = 4.2 Hz, IH), 7.43-7.69 <m, 4H); LCMS (M-l ): thiadiazole-5-carbothioamide 353.7
N-(4-bromo-2- 1 H-NMR (400 MHz, DMSO- ) δ 11.06 (s, IH), 7.85 (trifluoromethoxy)phenyl)-4- (d, / = 8.7 Hz, IH), 7.46-7.75 (m, 3H); LCMS (M-l ): (difluoromethyl)- 1 ,2,3 -thiadiazole - 5 - 417.8
carboxamide
N-(4-bromo-2- 1 H-NMR (400 MHz, DMSO-£¾ δ 12.80-12.37 (m, (trifluoromethoxy)phenyl)-4- IH), 7.69-7.78 (m, 3H), 7.49 (d, ./ = 53.0 Hz, IH); (difluoromethyl)- 1 ,2,3 -thiadiazole- 5 - LCMS (M-l): 433.7
carbothioamide
4-(difluoromethyl)-N-(3- 1 H-NMR (400 MHz, DMSO- ) δ 11.25 (s, IH), 7.80 (trifluoromethoxy)phenyl)- 1,2,3- (s, IH), 7.49-7.76 (m, 3H), 7.18 (dt, ,/ = 8.2, 1.1 Hz, thiadiazole-5-carboxamide IH)
4-(difluoromethyl)-N-(3- 1 H-NMR (400 MHz, DMSO- ) δ 12.79 (s, IH), 8.10 (trifluoromethoxy)phenyl)- 1,2,3- (s, IH), 7.80 (dd, J = 8.2, 0.8 Hz, I H), 7.47-7.74 (m, thiadiazole-5-carbothioamide 2H), 7.35-7.37 (m, IH) 71 4-(difluoromethyl)-N-methyl-N-(3- 1H-NMR (400 MHz, CDC13) δ 7.18-7.45 (m, 4H), (trifluoromethoxy)phenyl) - 1,2,3- 7.06-7.11 (m, 2H), 3.51 (s, 3H); LCMS (M-l): 353.27 thiadiazole-5-carboxamide
72 4-(difluoromethy 1 ) - N - methy 1 - N - ( 3 - Ή-NMR (400 MHz, CDC13) δ 7.36 (t, J = 8.2 Hz, I H), (trifluoromethoxy)phenyl)- 1,2,3- 7.00-7.27 (m, 4H), 3.84-3.90 (m, 3H); LCMS (M-l ): thiadiazole-5-carbothioamide 368.3
73 N-(2-chloro-5- Ή-NMR (400 MHz, DMSO- ) δ 11.02 (s, IH), 7.85 (trifluoromethoxy)phenyl)-4- (d, J = 2.1 Hz, IH), 7.49-7.75 (m, 2H), 7.36-7.39 (m, (difluoromethyl)- l,2,3-thiadiazole-5- IH); LCMS (M-l): 371.8
carbox amide
74 N-(2-chloro-5- Ή-NMR (400 MHz, DMSO- ) δ 12.85 (s, IH), 8.32 (trifluoromethoxy)phenyl)-4- (s, IH), 7.80-7.85 (m, 2H), 7.60 (t, J = 52,4 Hz, IH); (difluoromethyl)- l,2,3-thiadiazole-5- LCMS (M-l): 387.7
carbothioamide
75 N-(2,4-dichloro-5- Ή-NMR (400 MHz, DMSO- ) δ 11.10 (s, IH), 8.07 (trifluoromethoxy)phenyl)-4- (d, / = 4.7 Hz, 2H), 7.62 (t, / = 52.8 Hz, I H); LCMS (difluoromethyl)- l,2,3-thiadiazole-5- (M-l): 405.7
carboxamide
76 N-(2,4-dichloro-5- Ή-NMR (400 MHz, DMSO-^) δ 12.85 (s, IH), 8.08 (trifluoromethoxy)phenyl)-4- (d, ./ = 10.2 Hz, 2H), 7.70 (s, I H); LCMS (M-l): 421.7 (difluoromethyl)- l,2,3-thiadiazole-5- carbothioamide
77 N-(2-bromo-5- Ή-NMR (400 MHz, DMSO- ) ' 11 -34 (s, I H), 7.97 (trifluoromethoxy)phenyl)-4- (s, IH), 7.84 (d, J = 8.9 Hz, I H), 7.49-7.75 (m, 2H); (difluoromethyl)- l,2,3-thiadiazole-5- LCMS (M-l): 417.8
carbox amide
78 N-(2-bromo-5- Ή-NMR (400 MHz, DMSO- ) ' 12.85 (s, I H), 8.30 (trifluoromethoxy)phenyl)-4- (s, IH), 7.94 (d, J = 8.7 Hz, I H), 7.48-7.78 (m, 2H); (difluoromethyl)- l,2,3-thiadiazole-5- LCMS (M-l): 433.7
carbothioamide
79 N-(2,4-dibromo-5- Ή-NMR (400 MHz, DM. O- /,·, ) S 11.04 (s, I H), 8.30 (trifluoromethoxy)phenyl)-4- (s, IH), 7.95 (s, IH), 7.61 (t, / - 52.8 Hz, IH); LCMS (difluoromethyl)- 1 ,2,3-thiadiazole-5- (M-l): 495.7; LCMS (M-l): 379.9
carbox amide
80 N-(2,4-dibromo-5- Ή-NMR (400 MHz, f)MS( )■·· /., ) S 12.59 (s, I H), 8.31 (trifluoromethoxy)phenyl)-4- (s, I H), 7.98 (s, I H), 7.58-7.83 (m, I H); LCMS (M-l ): (difluoromethyl)- 1 ,2,3-thiadiazole-5- 511.07
carbothioamide
81 4-(difluoromethyl)-N-(4- Ή-NMR (400 MHz, OM$0~d6) d 1 1.17 (s, I H), (trifluoromethoxy)phenyl)- 1,2,3- 7.49-7.78 (m, 3H), 7.40 (d, / = 8.3 Hz, 2H)
thiadiazole-5-carboxamide
82 4-(difluoromethyl)-N-(4- 1H-NMR (400 MHz, DMSO- ) δ 12.72 (s, I H), 7.97 (trifluoromethoxy)phenyl)- 1 ,2,3 - (d, / = 9.0 Hz, 2H), 7.47-7.74 (m, 3H)
thiadiazole-5-carbothioamide
83 4-(difluoromethyl)-N-methyl-N-(4- 1H-NMR (400 MHz, DMSO- ) δ 7.38-7.66 (m, 5H), (trifluoromethoxy)phenyl)- 1,2,3- 3.39 (s, M l )
thiadiazole-5-carboxamide
84 4-(difluoromemyl)-N-methyl-N-(4- 1H-NMR (400 MHz, DMSO-ife) δ 7.33-7.59 (m, 5H), (trifluoromethoxy)phenyl)- 1,2,3- 3.83 (s, 3H)
thiadiazole-5-carbothioamide 85 N-(2-chloro-4- 1H-NMR (400 MHz, OMSO-d6) δ 11.15-10.84 (IH), (trifluoromethoxy)phenyl)-4- 7.88 (d, J = 8.9 Hz, IH), 7.56-7.82 (m, 2H), 7.45 (d, J (difluoromethyl)- 1 ,2,3-thiadiazoIe-5- - 8.9 Hz, IH)
carboxamide
86 N-(2-chloro-4- 'H-NMR (400 MHz, DMSO~d6) δ 12.69 (s, IH), 7.79 (trifluoromethoxy)phenyl)-4- (d, J = 8.6 Hz, 2H), 7.49-7.75 (m, 2H)
(difluoromethyl)- 1 ,2,3-thiadiazole-5- carbothioamide
87 N-(2-bromo-4- XH-NMR (400 MHz, DMSO- ) δ 11.01 (s, IH), 7.85 (trifluoromethoxy)phenyl)-4- (d, ./ = 2.3 Hz, IH), 7.77 (d, J = 8.7 Hz, IH), 7.62 (t, ./ = (difluoromethyl)- 1 ,2,3-thiadiazole-5- 52.9 Hz, IH), 7.53 (dd, J = 8.9, 1.5 Hz, I H)
carboxamide
88 N-(2-bromo-4- Ή-NMR (400 MHz, DMSO- ) δ 12.71 (s, IH), 7.90 (trifluoromethoxy)phenyl)-4- (d, J = 2.0 Hz, IH), 7.50-7.77 (m, 3H)
(difluoromethyl)- 1 ,2,3-thiadiazole-5- carbothioamide
89 N-(2-bromo-4- 'H-NMR (400 MHz, DMSO-t¾) δ 7.65-7.88 (m, 2H), (trifluoromethoxy)phenyl)-4- 7.44-7.57 (m, 2H), 3.31 (s, 3H); LCMS (M-l): 431.1 (difluoromethyl)-N-methyl- 1 ,2,3- thiadiazole-5-carboxamide
90 N-(2-bromo-4- Ή-NMR (400 MHz, DMSO-^) S 7.83 (d, J - 8.9 Hz, (trifluoromethoxy)phenyl)-4- IH), 7.72 (d, J = 1.1 Hz, IH), 7.45-7.61 (m, 2H), 3.73 (difluoromethyl)-N-methyl- 1 ,2,3- (s, 3H); LCMS (M-l ): 448.2
thiadiazole-5-carbothioamide
91 N-(3-(difluoromethoxy)phenyl)-4- Ή-NMR (400 MHz, DMSO-i¾) δ 11.15 (s, IH), (difluoromethyl)- 1 ,2,3-thiadiazole-5- 7.04-7.75 (m, 5H), 7.00 (d, J = 7.9 Hz, I H)
carboxamide
92 N - ( 3 - (dif 1 uorometh oxy )p heny 1 ) - 4 - Ή-NMR (400 MHz, f)MS( )■·· /., ) S 12.71 (s, I H), 7.84
(dif uoromethyl)- l,2,3-thiadiazole-5- (s, I H), 7.47-7.73 (m, 3H), 7.07-7.44 (m, 2H) carbothioamide
93 N-(3-(difluoromethoxy)phenyl)-4- Ή-NMR (400 MHz, DMSO-^) δ 7.01 -7.66 (m, 6H), (difluoromethyl)-N- methyl- 1 ,2,3- 3.35 (s, 3H); LCMS (M+l): 336.00
thiadiazole-5 -carboxamide
94 N-(3-(difluoromethoxy)phenyl)-4- ΊΙ- MR (400 MHz, 1 )MS( )- /,, ) δ 7.34-7.59 (m, 3H), (difluoromethyl)-N-methyl- 1,2,3- 6.98-7.32 (m, 3H), 3.82 (s, 3H); LCM S (M- l ): 352.00 thiadiazole-5-carbothioamide
95 N-(2,4-dichloro-5- 1H-NMR (400 MHz, DMSO--4 δ 1 1.05 (s, I H), 7.96 (difluoromethox y)phen y 1 )-4- (s, I H), 7.84 (s, IH), 7.62 (t, / = 53.0 Hz, IH), 7.28 (t, J (difluoromethyl)- 1 ,2,3-thiadiazole-5- = 72.7 Hz, IH); LCMS (M- l): 387.8
carboxamide
96 N-(4-(difluoromethoxy)phenyl)-4- Ή-NMR (400 MHz, DMSO- ) δ 11.09 (s, IH), (difluoromethyl)- 1 ,2,3-thiadiazole-5- 7.51-7.77 (m, 3H), 7.03-7.40 (m, 3H)
carboxamide
97 N-(4-(difluoromethoxy)phenyl)-4- Ή-NMR (400 MHz, DMSO- ) δ 12.64 (s, IH), 7.88 (difluoromethyl)- 1 ,2,3-thiadiazole-5- (d, J = 9.0 Hz, 2H), 7.60 (t, / = 5.6 Hz, IH), 7.09-7.46 carbothioamide (m, 3H)
98 N-(4-(difluoromethoxy)phenyl)-4- {H-NMR (400 MHz, DMSO-J6j δ 7.07-7.68 (m, 6H), (difluoromethyl)-N-methyl- 1 ,2,3- 3.36 (d, 7 = 5.0 Hz, 3H)
thiadiazole-5-carboxamide 99 N-(2-chloro-4- 1H-NMR (400 MHz, DMSO-ii6) δ 10.93 (s, IH),
(difluoromethoxy)phenyl)-4- 7.13-7.75 (m, 5H); LCMS (M-l): 353.85
(difluoromethyl)- 1 ,2,3-thiadiazoIe-5- carboxamide
100 4-(difluoromethyl)-N-(2- 'H-NMR (400 MHz, DMSO-^) δ 11.00 (s, IH),
(trifluoromethyl)phenyl)- 1 ,2,3- 7.77-7.84 (rn. 2H), 7.45-7.71 (m, 3H); LCMS(M-l): thiadiazole-5-carboxamide 321.9
101 4-(difluoromethyl)-N-(2- XH-NMR (400 MHz, DMSO-J5) δ 12.69 (d, J = 1.8
(trifluoromethyl)phenyl)- 1 ,2,3- Hz, IH), 7.44-7.87 (m, 5H); LCMS(M-l): 337.80 thiadiazole-5-carbothioaniide
102 N-(4-chloro-2- ¾-NMR (400 MHz, DMSQ-i¾) δ 11.01 (s, IH),
(trifluoromethyl)phenyl)-4- 7.85-7.89 (m, 2H), 7.41-7.74 (m, 2H); LCMS(M-l ): (difluoromethyl)- l,2,3-thiadiazole-5- 355.8
carboxamide
103 N-(4-chloro-2- ¾-NMR (400 MHz, DMSO-i¾) δ 12.70 (s, IH),
(trifluoromethyl)phenyl)-4- 7.48-7.92 (m, 4H); LCMS(M-l ): 371.80
(difluoromethyl)- 1 ,2,3 -thiadiazole - 5 - carbothioamide
104 N-(2,4-dichloro-6- ¾-NMR (400 MHz, DMSO-dtf) δ 11.42 (s, IH), 8.27
(trifluoromethyl)phenyl)-4- (d, J = 2.1 Hz, IH), 7.99 (d, J = 2.3 Hz, IH), 7.58 (t, J = (difluoromethyl)- 1 ,2,3 -thiadiazole - 5 - 53.0 Hz, IH); LCMS(M-l): 389.8
carbox amide
105 N-(4-bromo-2- Ή-NMR (400 MHz, DMSO- ) δ 1 1.03 (s, IH),
(trifluoromethyl)phenyl)-4- 8.06-7.98 (m, 2H), 7.69 (d, J = 9.2 Hz, IH), 7.58 (t, / =
(difluoromethyl)- l,2,3-thiadiazoIe-5- 53.0 Hz, IH)
carbox amide
106 N-(4-bromo-2- Ή-NMR (400 MHz, DMSO-i/6) δ 12.70 (s, IH), 8.04
(trifluoromethyl)phenyl)-4- (s, 2H), 7.48-7.75 (2H); LCMS(M-l): 389.75
(difluoromethyl)- l,2,3-thiadiazoIe-5- carbothioamide
107 N-(4-bromo-2- Ή-NMR (400 MHz, DMSO-,-/,,} δ 8.09-8.15 (m, 2H),
(trifluoromethyl)phenyl)-4- 7.85 (d, ,/ = 8.4 Hz, IH), 7.42-7.68 (m, IH), 3.34 (s,
(difluoromethyl)-N-methyl- 1 ,2,3- 3H); GCMS(M): 414.9
thiadiazole-5-carboxamide
108 4-(difluoromethyl)-N-(4-fluoro-2- Ή-NMR (400 MHz, DMSO-i ) δ 10.99 (s, IH),
(trifluoromethyl)phenyl)- 1 ,2,3- 7.74-7.78 (m, 2H), 7.44-7.70 (m, 2H); LCMS(M-l ); thiadiazole-5-carboxamide 339.8
109 4-(difluoromethyl)-N-(4-fluoro-2- ¾-NMR (400 MHz, DMSO- ) δ 12.66 (d, J - 4.7
(trifluoromethyl)phenyl)- 1 ,2,3- Hz, IH), 7.44-7.80 (m, 4H); LCMS(M-l): 355.80 thiadiazole-5-carbothioamide
110 1 H..NMR (400 MHz, DMSO..,d6) 6 11.30 (s, IH), S.13 (s, IH), 7.86 (d, J = 8.4 Hz,
4-(difluoromethyl)-N-(3-
(trifluoromethyl)phenyl)- 1 ,2,3- IH), 7.5i _7.77 (m, 3H)
thiadiazole-5-carboxamide
1 11 4-(difluoromethyl)-N-(3- 1H-NMR (400 MHz, DMSO-ifc) δ 12.84 (s, IH), 8.35
(trifluoromethyl)phenyl)- 1 ,2,3- (s, IH), 8.05 id, J = 6.7 Hz, IH), 7.50-7.76 (rn, 3H) thiadiazole-5-carbothioamide
1 12 4-(difluoromethyl) -N-methyl-N-(3 - ΊΙ- MR (400 MHz, DMSO-^) δ 7.39-7.84 (m, 5H),
(trifluoromethyl)phenyl)- 1 ,2,3- 3.44 (d, J = 12.8 Hz, 3H)
thiadiazole-5-carboxamide
113 N-(2-chloio-3- Ή-NMR (400 MHz, DMSO- ) δ 11.12 (s, I H), 8.00
(trifluoromethyl)phenyl)-4- (d, J = 7.8 Hz, IH), 7.83 (dd, J = 7.9, 1.2 Hz, IH), (difluoromethyl)- 1 ,2,3-thiadiazole-5- 7.49-7.76 (m, 2H); LCMS(M-l): 355.8
carboxamide
114 N-(2-chloro-3- Ή-NMR (400 MHz, OMSO-d6) δ 12.29 (s, I H),
(trifl uorometh yl)phen yl)-4- 7.58-7.92 (m, 4H); LCMS(M-l): 371.80
(difluoromethyl)- l,2,3-thiadiazole-5- carbothioamide
115 N-(4-chloro-3- Ή-NMR (400 MHz, DMSO--4 δ 1 1.37 (s, I H), 8.21
(trifl uorometh yl)phen yl)-4- (d, ,/ = 2.4 Hz, I H), 7.91 (dd, ,/ = 8.8, 2.4 Hz, IH), 7.76
(difluoromethyl)- l,2,3-thiadiazole-5- (d, J = 8.8 Hz, IH), 7.62 (t, / = 52.8 Hz, IH); LCMS carboxamide (M-l): 355.85
116 N-(4-chloro-3- ¾-NMR (400 MHz, DMSO- ) δ 12.88 (s, IH), 8.45 (trifluoromethyl)phenyl)-4- (d, J = 1.8 Hz, IH), 8.11 (dd, / = 8.6, 2.1 Hz, I H), 7.85 (difluoromethyl)- l,2,3-thiadiazoIe-5- (d, ,/ = 8.7 Hz, I H), 7.62 (t, J = 52.3 Hz, IH); carbothioamide LCMS(M-l): 371.75
117 4-(difluoromethyl)-N-(4- 1H-NMR (400 MHz, DMSO-rfi) δ 11.31 (s, IH), 7.87 (trifluoromethyl )phenyl .)- 1 ,2,3- (d, J - 8.6 Hz, 2H), 7.49-7.78 (m, 3H)
thiadiazole-5-carboxamide
118 4-(difluoromethyl)-N-(4- Ή-NMR (400 MHz, DMSO- ) δ 12.85 (s, IH), 8.09 (trifluoromethyl)phenyl)- 1 ,2,3- (d, ./ = 8.4 Hz, 2H), 7.86 (d, J = 8.6 Hz, 2H), 7.62 (t, / = thiadiazole-5-carbothioaniide 52.6 Hz, I H)
119 4-(difluoromethyl)-N-methyl-N-(4- Ή-NMR (400 MHz, DMSO- ) δ 7.76 (d, J - 6.3 Hz, (trifluoromethyl)phenyl)- 1 ,2,3- 2H), 7.41 -7.66 (m, 3H), 3.35-3.48 is, 3H ); GC S thiadiazole-5-carboxamide (M): 337.1
120 N-(2-chloro-4- 'H-NMR (400 MHz, DMSO- ) δ 11.07 (s, IH), 7.99 (trifluoromethyl)phenyl)-4- (d, ./ = 8.1 Hz, 2H), 7.80 (dd, ./ = 8.4, 1.7 Hz, IH), 7.60 (difluoromethyl)- 1 ,2,3-thiadiazoIe-5- (t, ,/ = 52.9 Hz, I H); LCMS (M-l): 335.8
carboxamide
121 N-(2-chloro-4- Ή-NMR (400 MHz, DMSO- ) δ 12.16 (s, IH), 8.03 (trifluoromethyl)phenyl)-4- (s, I H), 7.52-7.83 (m, 3H); LCMS(M-l): 371.80 (difluoromethyl)- 1 ,2,3-thiadiazoIe-5- carbothioamide
122 N-(2,6-dichloro-4- 1H-NMR (400 MHz, DMSO-rfi) δ 11.62 (s, IH), 8.15 (trifluoromethyl)phenyl)-4- (s, 2H), 7.63 (t, J = 52.9 Hz, IH); LCMS(M-l): 389.75 (difluoromethyl)- 1 ,2,3-thiadiazoIe-5- carboxamide
123 N-(2,6-dichloro-4- 'H-NMR (400 MHz, DMSO- ) δ 7.99-7.73 (m, 3H);
(trifluoromethyl)phenyl)-4- LCMS(M-l): 405.80
(difluoromethyl)- 1 ,2,3-thiadiazoIe-5- carbothioamide
124 N-(2-bromo-4- Ή-NMR (400 MHz, DMSO- ) δ 11.08 (s, IH), 8.14 (trifluoromethyl)phenyl)-4- (s, I H), 7.90 (dd, ,/ = 23.7, 8.4 Hz, 2H), 7.63 (t, J = 52.9 (difluoromethyl)- 1 ,2,3-thiadiazoIe-5- Hz, IH)
carboxamide
125 N-(2-bromo-4- 'H-NMR (400 MHz, DMSO- ) δ 8.17 (s, IH), (trifluoromethyl)phenyl)-4- 7.70-7.90 (m, 3H)
(difluoromethyl)- 1 ,2,3 -thiadiazole - 5 - carbothioamide
126 4-(difluoromethyl)-N-(2-fluoro-4- ¾-NMR (400 MHz, DMSO- ) δ 11.24 (s, IH), 8.15 (trifluoromethyl)phenyl)- 1 ,2,3- (t, ./ = 8.0 Hz, IH), 7.83 (dd, ./ = 10.7, 1.7 Hz, IH), thiadiazole-5-carboxamide 7.48-7.75 (m, 2H); LCMS(M-l): 339.85 127 4-(difluoromet yl)-N-(2-fluoro-4- 1H-NMR (400 MHz, DMSO-^) δ 12.75 (s, IH), (trifluoromethyl)phenyl)- 1 ,2,3- 7.88-7.97 (rn, 2H), 7.51-7.77 (m, 2H); LCMS(M-i): thiadiazole-5-carbothioaniide 355.80
128 N-(3,5-bis(trifluoromethyl)phenyl)- 'H-NMR (400 MHz, DMSO-di) δ 11.57 (s, IH), 8.31
4- (difluoromethyl)-l,2,3-thiadiazole- (s, 2H), 7.94 (s, IH), 7.65 (t, ./ = 52.7 Hz, IH);
5- carboxamide LCMS(M-l ): 389.85
129 N-(3,5-bis(trifluoromethyl)phenyl)- 1H-NMR (400 MHz, DMSO- ') δ 13.05 (s, I H), 8.51 4-(difluoromethyl)- 1 ,2,3-thiadiazole- (s, 2H), 8.09 (s, IH), 7.65 ( J = 52.3 Hz, IH);
5 -carbothioamide LCMS(M--l ): 405.85
130 4-(difluoromethyl)-N-(2-methyl-4- Ή-NMR (400 MHz, 1 )MS( )■·· /.,) δ 10.71 (s, IH),
(perfluoropropan-2-yl)phenyl)- 1 ,2,3- 7.52-7.81 (m, 4H), 2.34 (s, 3H); LCMS (M-l): 435.8 thiadiazole-5-carboxamide
131 N-(2-chlorophenyl)-4- 'H-NMR (400 MHz, DMSO-i¾) δ 10.90 (s, IH),
(difluoromethyl)- 1 ,2,3 -thiadiazole - 5 - 7.47-7.75 (m, 3H), 7.42 (td, J = 7.6, 1.5 Hz, IH), 7.34 carboxamide (td, ,/ = 7.7, 1 .5 Hz, I H); LCMS (M-l): 288.6
132 N-(2-chlorophenyl)-4- Ή-NMR (400 MHz, DMSO- ) δ 12.61 (s. IH),
(difluoromethyl)- 1 ,2,3-thiadiazole-5- 7.42-7.73 (m, 5H); LCMS (M- l): 304.74
carbothioamide
133 N-(2,4-dichlorophenyl)-4- Ή-NMR (400 MHz, DMSO-J6) δ 10.94 (s, IH), (difluoromethyl)- 1 ,2,3-thiadiazole-5- 7.48-7.76 (m, 4H); LCMS (M-l): 321.8
carboxamide
134 N-(2,4-dichlorophenyl)-4- Ή-NMR (400 MHz, DMSO-^) δ 12.70 (d, J = 11.0 (difluoromethyl)- 1 ,2,3-thiadiazole-5- Hz, IH), 7.51-7.83 (m, 4H); LCMS (M-l V 75 carbothioamide
135 4-(difluoromethyl)-N-(2,4,6- Ή-NMR-NMR (400 MHz, DMSO- ') δ 1 1.35 (s, trichlorophenyl)- 1 ,2,3-thiadiazole-5- IH), 7.88 (s, 2H), 7.61 (t. ./ = 53.0 Hz, IH); LCMS carboxamide (M- l): 357.56
136 4-(difluoromethyl)-N-(2,4,6- Ή-NMR-NMR (400 MHz, DMSO- ) δ 13.28-12.28 trichlorophenyl)- 1 ,2,3-thiadiazole-5- (IH), 7.85 is, 2H), 7.51-7.78 (m, I H); LCMS (M-l ): carbothioamide 373.63
137 N-(2,3-dichlorophenyl)-4- ¾-NMR (400 MHz, DMSQ-i¾) δ 11.06 (s, IH),
(difluoromethyl)- 1 ,2,3-thiadiazole-5- 7.43-7.76 (m, 4H); LCMS (M-l ): 321.80
carboxamide
138 N-(2,3-dichlorophenyl)-4- Ή-NMR (400 MHz, DMSO-^) δ 12.74 (s, IH),
(difluoromethyl)- 1 ,2,3-thiadiazole-5- 7.47-7.77 (m, 4H); LCMS (M-l): 337.75
carbothioamide
139 N-(2,5-dichlorophenyl)-4- Ή-NMR-NMR (400 MHz, DMSO-ii6) δ 11.01 (s,
(difkioromethyl)- 1 ,2,3 -ihiadiazole-5- IH), 7.88 (d, J = 2.3 Hz, IH), 7.49-7.76 (m, 2H), 7.42 carboxamide (dd, / = 8.6, 2.5 Hz, IH); LCMS (M-l ): 323.12
140 N-(2-chloro-4-methylphenyl)-4- Ή-NMR (400 MHz, DMSO ·· /,, ;· δ 10.83 (s, I H), 7.61 (difluoromethyl)- 1 ,2,3-thiadiazole-5- (s, IH), 7.53 (d, J = 8.1 Hz, IH), , 7.41 (d, J = 0.9 Hz, carboxamide IH), 7.22 (dd, / = 8.1, 1.2 Hz, IH), 2.32 (s, 3H); LCMS
(M-l): 301.8
141 N-(3-chlorophenyl)-4- 'H-NMR (400 MHz, DMSO-J6j δ 1 1.16 (s, IH), 7.85 (difluoromethyl)- 1 ,2,3-thiadiazole-5- (t, J = 2.0 Hz, IH), 7.50-7.76 (rn. 2H), 7.43 (t, J 8.1 Hz, carboxamide IH), 7.25 (dq, J = 8.0, 1.0 Hz, IH); LCMS(M-l):
287.85
142 N-(3-chlorophenyl)-4- 1H-NMR (400 MHz, DMSO-i¾) δ 8.07 (s, IH), (difluoromethyl)- 1 ,2,3-thiadiazole-5- 7.40-7.74 (m, 5H). LCMS (M-l ); 303.8
carbothioamide 143 N-(3,4-dichlorophenyl)-4- 1H-NMR-NMR (400 MHz, DMSO~d6) δ 11.26 (s,
(difluoromethyl)- l,2,3-thiadiazoIe-5- IH), 8.02 (d, J = 2.3 Hz, 1 H), 7.49-7.75 (m, 3H);
carbox amide LCMS (M- l): 323.12
144 N-(3,4-dichlorophenyl)-4- Ή-NMR (400 MHz, OM$0~d6) δ 12.79 (s, IH), 8.28
(difluoromethyl)- 1 ,2,3-thiadiazole-5- (s, IH), 7.48-7.79 (m, 3H); LCMS (M-l): 339.18 carbothioamide
145 N-(3,5-dichlorophenyl)-4- 'H-NMR-NMR (400 MHz, OUSO-d6) δ 11.28 (s,
(difluoromethyl)- l,2,3-thiadiazoIe-5- IH), 7.49-7.75 (m, 3H), 7.44 (t, J - 1.8 Hz, IH).
carboxamide
146 N-(3-chloro-4-methylphenyl)-4- 1 H-NMR-NMR (400 MHz, DMSO-d6) δ 1 1 .07 (s, (difluoromethyl)- l,2,3-thiadiazole-5- IH), 7.83 (d, J - 1.8 Hz, IH), 7.62 (i, J = 52.8 Hz, IH), carboxamide 7.45 (dd, J = 8.3, 2.0 Hz, I H), 7.36 (d, J = 8.4 Hz, IH),
2.30 (s, 3H); LCMS (M- l): 302.71
147 N-(3-chloro-4-methylphenyl)-4- 'H-NMR-NMR (400 MHz, DMSO-<¾) δ 12.78 (s,
(difluoromethyl)- l,2,3-thiadiazoIe-5- IH), 8.19 (d, J - 1.7 Hz, IH), 7.59-7.87 (m, 3H), 2.64 carbothioamide (s, 3H); LCMS (M-i ): 318.77
148 N-(4-chlorophenyl)-4- Ή-NMR-NMR (400 MHz, D.MSO-, ,, ) 11.11 (s,
(difluoromethyl)- 1 ,2,3-thiadiazole-5- I H), 7.48-7.75 (m, 3H), 7.45 (dd, / = 6.8, 2.1 Hz, 2H); carboxamide LCMS (M-l): 288.68
149 N-(4-chlorophenyl)-4- Ή-NMR (400 MHz, OMSO-d6) δ 12.68 (s, I H),
(difkioromethyl)- 1 ,2,3 -ihiadiazole-5- 7.87-7.91 (m, 2H), 7.47-7.73 (m, 3H); LCMS (M-l): carbothioamide 304.76
150 N-(2-bromophenyl)-4- ' H-NMR (400 MHz, OMSO-d6) δ 10.90 (s, I H),
(difluoromethyl)- 1 ,2,3-thiadiazole-5- 7.44-7.75 (m, 4H), 7.26-7.30 (m, IH); LCMS (M-l): carboxamide 331.80
151 N-(2-bromophenyl)-4- ' H-NMR (400 MHz, DMSO- δ 12.64 (s, I H), 7.80
(difluoromethyl)- 1 ,2,3-thiadiazole-5- (d, J = 7.8 Hz, IH), 7.50-7.63 (m, 3H), 7.36 (t, / = 7.3 carbothioamide Hz, IH); LCMS (M-l): 349.75
152 N-(2-bromo-5-chlorophenyl)-4- 1 H-NMR (400 MHz, DMSO- ) δ 11.00 (s, IH),
(difluoromethyl)- 1 ,2,3-thiadiazole-5- 7.60-7.90 (m, 3H), 7.25 (dd, ./ - 8.5, 2.1 Hz, IH); carbox amide LCMS (M- l): 217.8
153 N-(2-bromo-5-chlorophenyl)-4- 1 H-NMR (400 MHz, DMSO-^) δ 12.22 (IH),
(difluoromethyl)- 1 ,2,3-thiadiazole-5- 7.56-7.82 (m, 3H), 7.38 (d, J = 6.7 Hz, IH); LCMS carbothioamide (M-l): 383.75
154 N-(2,4-dibromophenyl)-4- 1 H-NMR (400 MHz, DMSO- ) δ 10.93 (s, IH), 8.00
(difluoromethyl)- 1 ,2,3-thiadiazole-5- (d, J = 2.3 Hz, I H), 7.48-7.75 (m, 3H); LCMS (M-l): carboxamide 411.75
155 N-(2,4-dibromophenyl)-4- 'H-NMR (400 MHz, OMSO-de) δ 12.69 (s, IH), 8.05
(difkioromethyl)- 1 ,2,3 -ihiadiazole-5- (s, IH), 7.56-7.71 (m, 3H); LCMS (M-l): 427.70 carbothioamide
156 4-(difluoromethyl)-N-(2,4,6- 'H-NMR (400 MHz, DMSO-i/6) δ 11.39 (s, IH), 8.12 tribromophenyl)- 1 ,2,3-thiadiazole-5- (s, 2H), 7.61 it, ./ = 52.8 Hz, I H); LCMS (M-l): 489.65 carboxamide
157 N-(2-bromo-4-fluorophenyl)-4- 1 H-NMR (400 MHz, DM SO--4 δ 10.91 (s, IH), (difluoromethyl)- l,2,3-thiadiazoIe-5- 7.48-7.74 (m, 3H), 7.36 (td, J - 8.6, 2.9 Hz, IH); carboxamide LCMS (M- l): 349.75
158 N-(2-bromo-4-fl.uorophenyl)-4- 'H-NMR-NMR (400 MHz, DMSO-i/6) δ 12.62 (s,
(difluoromethyl)- 1 ,2,3-thiadiazole-5- I H), 7.43-7.80 (m, 4H); LCMS (M-l ): 368.19 carbothioamide 159 N-(2-bromo-3-methylphenyl)-4- 1H-NMR (400 MHz, OMSO-d6) δ 10.89 (s, IH), 7.62 (difluoroniethyi)~ l,2,3"thiadiazoIe-5- (t, J = 52.9 Hz, IH), 7.33-7.43 (m, 3H), 2.41 (s, 3H); carbox amide LCMS (M- l): 345.8
160 N-(3 - bromopheny 1 )-4- Ή-NMR (400 MHz, OM$0~d6) δ 11.16 (s, IH), 7.98 (difluoromethyl)- 1 ,2,3-thiadiazole-5- (d, J = 1.8 Hz, IH), 7.49-7.75 (m, 2H), 7.33-7.39 (m, carboxamide 2H); LCMS (M-l): 331.8
161 N-(3 -bromo phenyl )-4- 1H-NMR (400 MHz, DMSO- ) δ 12.73 (s, IH), 8.15 (difluoromethyl)- 1 ,2,3-thiadiazole-5- (s, IH), 7.41 -7.77 (rn, 4H); LCMS (M-l): 349.75 carbothioamide
162 N-(4 -bromophenyl )-4- Ή-NMR (400 MHz, DM . SO ·· /,, } S 11.11 (s, IH), (difluoromethyl)- 1 ,2,3-thiadiazole-5- 7.49-7.75 (m, 5H); LCMS (M-l): 333.75
carboxamide
163 4-(difluoromethyl)-N-(2- 'H-NMR (400 MHz, DMSO-i 6) δ 10.96 (s, IH), 7.79 fluorophenyl)- 1 ,2,3-thiadiazole-5- (t, J = 7.3 Hz, IH), 7.61 (i, / = 53.0 Hz, IH), 7.23-7.35 carboxamide (m, 3H); LCMS (M- l): 271 .8
164 4-(difluoromethyl)-N-(2- ΊΙ- MR (400 MHz, DMSO- ) 0 12.53 (s, IH), iluorophenyl)- 1 ,2,3-thiadiazole-5- 7.48-7.74 (m, 2H), 7.28-7.46 (m, 3H); LCMS (M- l): carbothioamide 287.5
165 N-(4-chloro-2-fluorophenyl.)-4- 1H-NMR (400 MHz, DMSO-i¾ δ 11.07 (IH), 7.81 (t, (difluoromethyl)- 1 ,2,3-thiadiazole-5- J = 8.5 Hz, I H), 7.48-7.74 (m, 2H), 7.35 (dq, ./ = 8.7, carboxamide 1.1 Hz, I H); LCMS (M- l): 305.8
166 N-(4-chloro-2-fluorophenyl)-4- Ή-NMR-NMR (400 MHz, DMSO- ) δ 12.56 (s,
(difkioromethyl)- 1 ,2,3 -ihiadiazole-5- IH), 7.60-7.87 (m, 2H), 7.53 (d, J = 10.2 Hz, IH), 7.33 carbothioamide (d, J = 8.3 Hz, IH); LCMS (M-l ): 322.73
167 N-(3-chloro-2-fluorophenyl)-4- Ή-NMR (400 MHz, DMSO-i/6) ' 1 K ! 3 (s, IH),
(difluoromethyl)- l,2,3-thiadiazole-5- 7.48-7.76 (m, 3H), 7.29 (id, ./ = 8.2, 1.5 Hz, IH);
carboxamide LCMS (M-l): 305.80
168 N-(3-chloro-2-fluorophenyl)-4- XH-NMR (400 MHz, DMSO- ) δ 12.67 (s, IH),
(difluoromethyl)- l,2,3-thiadiazoIe-5- 7.49-7.75 (m, 3H), 7.35 (td, J - 8.1, 1.2 Hz, IH); carbothioamide LCMS (M- l): 321 .75
169 N-(4-bromo-2-fl.uorophenyl)-4- Ή-NMR (400 MHz, DMSO- ) <·>' i i .03 (s, I H), 7.80 (difluoromethyl)- 1 ,2,3-thiadiazole-5- (t, J = 8.5 Hz, IH), 7.46-7.75 (m, 3H); LCMS (M-l): carboxamide 351 .75
170 N-(4-bromo-2-fl.uorophenyl)-4- Ή-NMR (400 MHz, DMSO- ) d 12.55 (s, I H), 7.76 (difluoromethyl)- 1 ,2,3-thiadiazole-5- (dd, J = 9.9, 2.1 Hz, I H), 7.46-7.73 (m, 3H); LCMS carbothioamide (M-l): 367.70
171 N-(3-bromo-2-fluorophenyl)-4- Ή-NMR (400 MHz, DMSO-i¾) δ 11.11 (s, I H), 7.78
(difkioromethyl)- 1 ,2,3 -ihiadiazole-5- (i, J = 7.1 Hz, IH), 7.48-7.75 (m, 2H), 7.22 (td, 7 = 8.1, carboxamide 1.3 Hz, I H); LCMS (M- l): 349.80
172 N-(3-bromo-2-fluorophenyl)-4- Ή-NMR (400 MHz, i)MS( )···,·/,, ) d 12.65 (s, I H),
(difluoromethyl)- l,2,3-thiadiazole-5- 7.48-7.76 (m, M l ). 7.28 (t, ./ = 8.0 Hz, IH); LCMS carbothioamide (M-l): 367.75
173 4-(difluoromethyl)-N-(2,6- XH-NMR (400 MHz, DMSO- ) δ 11.06 (s, IH), difluorophenyl)- 1 ,2,3 -thiadiazoIe--5- 7.41-7.71 (m, 2H), 7.23 (t, J = 8.3 Hz, 2H); LCMS carbox amide (M-l ): 289.85
174 4-(difluoromethyl)-N-(2,6- Ή-NMR (400 MHz, DMSO-i ) δ 12.51 (s, IH), 7.65 difluorophenyl)- 1 ,2,3-thiadiazole-5- (t, J - 53.1 Hz, IH), 7.46 (m, IH), 7.25 (t, J = 8.4 Hz, carbothioamide 2H); LCMS (M-l): 305.75 175 4-(difluoromethyl)-N-(2-fluoro-4- 1H-NMR (400 MHz, DMSO-i¾s) δ 10.85 (s, i H i. methylphenyl)- 1 ,2,3-thiadiazole-5- 7.47-7.73 (m, 2H), 7.15 (d, J = 1 1.8 Hz, 1 H), 7.05 (d, J carbox amide = 8.1 Hz, 1H), 2.31 (s, 3H); LCM S (M- l ): 285.85
176 4-(difluoromethyl)-N-(3- Ή-NMR (400 MHz, 1 )N1S( ) ·· /,, } 0 11.15 (s, I I I ). fluorophenyl)- 1 ,2,3-thiadiazole-5- 7.36-7.73 (m, 4H), 6.97-7.02 (m, IH); LCMS (M-l): carboxamide 271 .85
177 4-(difluoromethyl)-N-(3- Ή-NMR (400 MHz, OMSO-d6) δ 12.74 (s, IH), 7.93 fluorophenyl)- 1 ,2,3-thiadiazole-5- (dt, ,/ = 10.9, 2.1 Hz, IH), 7.47-7.73 (m, 3H), carbothioamide 7.18-7.23 (m, IH) ; LCMS (M-l): 287.80
178 4-(difluoromethyl)-N-(3,4- Ή-NMR (400 MHz, DMSO-4) δ 11.20 (s, I H), 7.80 difluorophenyl)- 1 ,2,3-thiadiazole-5- (ddd, J = 12.8, 7.4, 2.4 Hz, I H), 7.39-7.75 (m, 3H); carboxamide LCMS (M-l ): 289.85
179 4 - (difluoromethy 1 j - N - ( 3,4- Ή-NMR (400 MHz, OM$0~d6) δ 12.73 (s, I H), difluorophenyl)- l,2,3-thiadiazole-5- 8.06-8.11 (m, IH), 7.48-7.74 (m, 3H); LCMS (M-l): carbothioamide 305.75
180 4-(difluoromethyl)-N-(4- 1H-NMR (400 MHz, DMSO- ) δ 11.13 (s, IH),
fluorophenyl)- 1 ,2,3-thiadiazole-5- 7.49-7.75 (m, 3H), 7.21-7.26 (m, 2H); LCMS(M-l ): carboxamide 271.8
181 4-(difluoromethyl)-N-(4- Ή-NMR (400 MHz, DMSO- ) δ 12.62 (s, IH), fluorophenyl)- 1 ,2,3-thiadiazole-5- 7.84-7.88 (m, 2H), 7.60 (t, J = 52.6 Hz, IH), 7.29-7.35 carbothioamide (m, 2H); LCMS (M- l): 287.80
182 N-(4-bromo-2-methylphenyl)-4- SH--NMR (400 MHz, DMSO- ) δ 10.56 (s, IH),
(difluoromethyl)- 1 ,2,3-thiadiazole-5- 7.48-7.74 (m, 2H), 7.41 (d, J = 2.9 Hz, 2H), 2.20 (s, carboxamide 3H); LCMS (M-l): 345.80
183 N-(4-bromo-2-meth ylphen yl)-4- 1H-NMR (400 MHz, DMSO-i¾ δ 12.35 (s, IH),
(difluoromethyl)- 1 ,2,3-thiadiazole-5- 7.50-7.77 i m. 3H), 7.39 id, ./ = 8.4 Hz, I H), 2.23 (s, carbothioamide 3H); LCMS (M-l): 363.75
184 4-(difluoromethyl)-N-(4-fluoro-2- ' H-NMR (400 MHz, DMSO- ) δ 10.56 (s, I H), 7.64 methylphenyl)- 1 ,2,3-thiadiazol.e-5- 0, J = 53.0 Hz, IH), 7.45 (dd, / = 8.8, 5.6 Hz, IH), 7.16 carboxamide (dd, J - 9.7, 2.8 Hz, IH), 7.08 (id, J = 8.6, 3.1 Hz, IH),
2.24 (s, 3! 15: LCMS (M-l): 285.71
185 4-(difluoromethyl)-N-(4-fluoro-2- 1 H-NMR (400 MHz, DMSO- ) δ 12.30 (s, IH), 7.64 methylphenyl)- 1 ,2,3-thiadiazole-5- (t, J = 52.7 Hz, IH), 7.45 (dd, ,/ = 8.7, 5.7 Hz, I H), 7.23 carbothioamide (dd, / = 9.7, 2.8 Hz, I H), 7.15 (td, ./ = 8.6, 2.9 Hz, IH),
2.24 (s, 3H); LCMS (M-l): 301.85
186 4-(difluoromethyl)-N-(p-tolyl)- 1 ,2,3- 1 H-NMR (400 MHz, DMSO--4 δ 10.92 (s, I H),
thiadiazole-5-carboxamide 7.48-7.75 (m, 3H), 7.19 (d, J = 8.3 Hz, 2H), 2.28 (s,
3H); LCMS (M-l ): 267.85
187 4-(difluoromethyl)-N-(p-tolyl)- 1 ,2,3- 1 H-NMR (400 MHz, DMSO- ) δ 12.52 (s, IH),
thiadiazole-5-carbothioamide 7.45-7.73 (m, 3H), 7.27 (d, / = 8.1 Hz, 2H), 2.32 (s,
3H); LCMS (M-l): 283.85
188 4-(difluoromethyl)-N- ' H-NMR-NMR (400 MHz, DMSO-<¾j) δ 1 1 .50 (s,
(perfl.uorophenyl)- 1 ,2,3-thiadiazole- IH), 7.61 (t, J = 53.0 Hz, IH); LCMS (M-l): 344.19
5-carboxamide
189 4-(difluoromethyl)-N- 1 H-NMR-NMR (400 MHz, DMSO- ) δ 7.87 (t, J -
(perfluorophenyl)- 1 ,2,3-thiadiazole- 53.5 Hz, I H), 3.81-3.84 (m, I H); LCMS (M-l): 5-carbothioamide 359.80
190 4-(difluoromethyl)-N-(2,3,5,6- 1 H-NMR (400 MHz, DMSO-i¾) δ 1 1 .52 (s, I H), tetrafluorophenyl)- 1 ,2,3-thiadiazole- 7.93-7.99 (m, IH), 7.61 ft, J = 53.0 Hz, IH); LCMS
5-carboxamide (M- l): 325.80 191 4- (dffluoromethyl)-N-(2,3,5,6- 1H-NMR (400 MHz, DM SO--,/,, ) δ 8,58 (t, 7 = 53.1 Hz, tetrafluorophenyl)- 1 ,2,3 -thiadiazole- 2H); ί .C. S (M-i): 341.80
5- carbothioamide
192 N-(2-cyanophenyl.)-4- Ή-NMR-NMR (400 MHz, DMSO- ) δ 11.42 (s,
(difluoromethyl)- l,2,3-thiadiazole-5- IH), 7.92 (dd, 7 = 7.8, 1.2 Hz, I H), 7.47-7.81 (m, 4H); carboxamide LCMS (M-l): 278.80
193 N-(4-chloro-2-methoxyphenyl)-4- 1 H-NMR (400 MHz, DMSO-d6) δ 10.48 (s, IH), 7.79 (difluoromethyl)- 1 ,2,3 -thiadiazole - 5 - (d, 7 = 8.4 Hz, IH), 7.56 (t, 7 = 53.0 Hz, I H), 7.17 (d, 7 carboxamide = 2.0 Hz, IH), 7.03 (dd, 7 = 8.6, 2.3 Hz, IH), 3.81 (s,
3H); LCMS (M-l ): 317.85
194 N-(4-chloro-2-methoxyphenyl)-4- Ή-NMR (400 MHz, DN1SO -//,, } 0 12.25 (s, IH), (difluoromethyl)- 1 ,2,3-thiadiazole-5- 7.39-7.68 (m, 2H), 7.29 (d, ,/ = 2.1 Hz, IH), 7.12 (dd, ./ carbothioamide = 8.4, 2.1 Hz, IH), 3.85 (s, 3H); LCMS (M-l): 333.80
195 4-(difluoromethyl)-N-(3- Ή-NMR (400 MHz, DMSO-4) δ 10.97 (s, I H), 7.62 methoxyphenyl)- 1 ,2,3-thiadiazole-5- 0, 7 = 52.9 Hz, IH), 7.27-7.32 (m, 2H), 7.20-7.23 (m, carboxamide IH), 6.76 (ddd, 7 = 8.2, 2.5, 0.9 Hz, IH), 3.75 (s, 3H)
196 4-(difluoromethyl)-N-(3- ' H-NMR (400 M Hz, DMSO -Y/,, ) δ 12.57 (s, I H), methoxyphenyl.)- 1 ,2,3-thiadiazole-5- 7.45-7.72 (m, 2H), 7.38-7.39 (m, 2H), 6.91-6.94 (m, carbothioamide IH), 3.76 (s, 3H)
197 N-(2-chloro-3-methoxyphenyl)-4- 1 H-NMR (400 MHz, DMSO-d6) δ 10.85 (s, I H), 7.61 (difl.uoromethyl)- 1 ,2,3-thiadiazole-5- (t, 7 = 53.0 Hz, IH), 7.37 (t, 7 = 8.2 Hz, IH), 7.28 (d, 7 carboxamide = 7.8 Hz, I H), 7.11 (d, 7 = 8.3 Hz, I H), 3.88 (s, 3H)
198 4-(difluoromethyl)-N-(4- ! H-NMR (400 MHz, DMSO -//,, ; .·) 10.87 (s, I H), methoxyphenyl.)- 1 ,2,3-thiadiazole-5- 7.48-7.74 (m, 3H), 6.95 (dd, 7 - 6.9, 2.1 Hz, 2H), 3.74 carboxamide (s, 3H)
199 4-(difluoromethyl)-N-(4- ! H-NMR (400 MHz, DMSO -//,, ; .·) 12,48 (s, I H), methoxyphenyl.)- 1 ,2,3-thiadiazole-5- 7.76-7.80 (m, 2H), 7.58 (t, ,/ - 52.7 Hz, IH), carbothioamide 7.00-7.04 (m, 2H), 3.78 (s, 3H)
200 N-(2-chloro-4-methoxyphenyl)-4- 'H-NMR-NMR (400 MHz, DMSG-i¾ δ 10.76 (s, (difluoromethyl)- 1 ,2,3-thiadiazole-5- IH), 7.48-7.74 (m, 2H), 7.16 (d, 7 = 2.8 Hz, IH), 6.99 carboxamide (dd, 7 = 8.9, 2.8 Hz, IH), 3.79 (s, 3H); LCMS (M-l):
318.71
201 N-(2-chloro-4-methoxyphenyl)-4- 1 H-NMR (400 MHz, DMSO -//,, } δ 12.41 (s, IH), (difluoromethyl)- 1 ,2,3-thiadiazole-5- 7.41-7.68 (m, 2H), 7.18 (d, 7 = 2.8 Hz, IH), 7.01 (dd, 7 carbothioamide = 8.8, 2.8 Hz, I H), 3.78 (s, 3H); LCMS (M-l): 333.80
202 N-(2-chloro-4-(pentafluoro-16- 'H-NMR (400 MHz, DMSO- ) δ 12.47 (s, I H), 8.28 sulfaneyl)phenyl)-4-methyl- 1 ,2,3- (s, IH), 8.04 (dd, 7 = 8.9, 1.8 Hz, IH), 7.86 (d, 7 = 8.1 thiadiazole-5-carbothioamide Hz, IH), 2.83 (s, 3H)
203 4-methyl-N-(3- 'H-NMR (400 MHz, D MSO -,/,, ) /) 12.41 (s, I H), 8.29
((trifluoromethyl)thio)phenyl)- 1,2,3- (s, IH), 8.00 (d, 7 = 7.5 Hz, IH), 7.59-7.66 (m, 2H), thiadiazole-5-carbothioamide 2.71 I s. M l )
204 4-methyl-N-(4- ' H-NMR (400 MHz, CDC13) δ 9.29 (s, I H), 7.81 (dd,
((trifluoromethyl)thio)phenyl)- 1 ,2,3- 7 = 61.4, 8.2 Hz, 4H), 2.83 (s, 3H)
thiadiazole-5-carbothioamide
205 4-methyl-N-(3- 1 H-NMR (400 MHz, DMSQ-i¾) δ 12.45 (s, IH), 8.09
(trifluoromethoxy)phenyl)- 1,2,3- (s, I H), 7.82 (d, 7 = 8.1 Hz, I H), 7.61 (t, ./ - 8.3 Hz, thiadiazole-5-carbothioamide I H), 7.34 (d, 7 = 8.3 Hz, IH), 2.74 (s, 3H)
206 4-methyl-N-(4- 1 H-NMR (400 MHz, DMSO-i¾ δ 12.38 (s, IH),
(trifluoromethoxy)phenyl)- 1,2,3- 7.95-7.98 (m, 2H), 7.48 (d, 7 = 8.4 Hz, 2H), 2,74 (s, thiadiazole-5-carbothioamide 3H)
Figure imgf000103_0001
223 N-(5-bromo-2-chloropyridin-3-yl)-4- 1H-NMR (400 MHz, DMSO-rfi) δ 11.18 (s, IH), 8.51 (difluoromethyl) - 1 ,2,3 -thiadiazole - 5 - (s, 2H), 7.63 (t, 7 = 52.7 Hz, IH).
carbothioamide
224 N-(3-chloro-5- Ή-NMR (400 MHz, DMSO- ) '> 11.99 (s, I H), 8.86
(trifluoromethyl)pyridin-2-yl)-4- (s, IH), 8.64 (d, J = 1.7 Hz, IH), 7.62 (t, J = 53.0 Hz, (difluoromethyl)- 1 ,2,3 -thiadiazole - 5 - IH); LCMS (M-I): 356.8
carbothioamide
225 4-meth yl -N-(3 '-(pen tafluoro-16- Ή-NMR (400 MHz, DMH -d,,) δ 10.49 (s, I H), sulf aneyl)- [ 1 , 1 '-biphenyl] -2-yl)- 7.92-7.85 (m, IH), 7.81 (s, I H), 7.74-7.63 (m, 2H), 1,2, 3 - thiadiazole- 5 -c arbo thioamide 7.52 (t, 7 = 3.4 Hz, 2H), 7.50-7.43 (m, 2H), 2.58 (s,
3H)
226 4-isopropyl-N-(3'-(pentafluoro-16- Ή-NMR (400 MHz, OMSO-d6) δ l().5(s, IH), 7.91 sulfaneyl)-[ l ,l'-biphenyl]-2-yl)- (m, IH), 7.81 (s, I H), 7.96 (d, J = 5.2 Hz, 2H),
1 ,2, 3 -thiadiazole- 5 -carbo thioamide 7.53-7.52 (m, 2H), 7.47-7.46 (m, 2H), 3.29 (m, IH),
1.27 (d, 6H); LCMS (M-l): 448.35
4-isopropyl-N-methyl-N-(3'- 1H-NMR (400 MHz, OMSO-d6) S 7.9.1 (d, ./ = 8.4 Hz, (pentafluoro-16-sulfaneyl )-[ 1 ,1'- IH), 7.75 (d, , J = 1.2 Hz, IH), 7.64-7.62 (m, 3H), bipheny 1 ] - 2- yl) - 1 , 2 ,3 -thiadiazole- 5 - 7.46-7.43 (m, 2H), 7.27 (d, J = 8Hz, IH), 3.46 (s, 3H), carbothioamide 3.1 (m, IH), 1.14 (d, 3H), 0.95 (d, 3H); LCMS (M+1):
464.15
228 4-(difluoromethyl) -N-(3 ' - Ή-NMR (400 MHz, DM SO-,/,. I ·-> 10.81 (s, IH), (pentafluoro-16-sulfaneyl)- [ 1 , 1 '- 7.92-7.86 (m, IH), 7.83 (t, J = 2.1 Hz, I H), 7.76-7.64 biphenyl] -2-yl)- 1 ,2,3 -thiadiazole- 5- (m, 2H), 7.61 (d, J = 7.3 Hz, IH), 7.57-7.18 (m, 3H), carbothioamide 7.35 (t, 7 = 52.6 Hz, IH)
229 4-(difluoromethyl)-N-(3'- Ή-NMR (400 MHz, DMSO-i¾) δ 12.53 (s, I H), 7.95 (pentafluoro-16-sulfaneyl)- [1 ,1 '- (d, 7 = 7.9 Hz, IH), 7.84 (s, IH), 7.67-7.72 (m, 2H), biphen l ] - 2- yl) - 1 , 2 ,3 -thiadiazole- 5 - 7.56 (d, 7 = 11.2 Hz, 4H), 7.32 (t, ,/ = 52.7 Hz, I H). carbothioamide
230 (E)-N-(2-(N-cyano-S- 1H-NMR (400 MHz, DMSO-i ) δ 8.34 (t, 7 = 1 .8 Hz, isopropy 1 sul.fi ni niido yl)phen yl) -4- IH), 8.15-8.04 (m, IH), 7.83 (t, 7 = 7.8 Hz, IH), methyl- 1 ,2,3-thiadiazole-5- 7.81 -7.75 (m, I H), 2.99 (s, 3H), 3.98 (septet, 7 = 6.6 carboxamide Hz, IH), 1.30 (d, 7 = 6.9 Hz, 3H), 1.21 (d, 7 = 6.9 Hz,
3H)
231 N-(4'-(N-ethyl-S- 1H-NMR (400 MHz, DMSO -Y/,, ) δ 10.46 (s, I H), 7.88 niethyl.sulfonimidoyl.)-[ 1,1 '- (d, J = 8.2 Hz, 2H), 7.63 (d, J = 7.8 Hz, 2H), 7.46-7.56 biphenyl]-2-yl)-4-m.ethyl- l,2,3- (m, 4H), 3.13 (s, 3H), 2.80-2.89 (m, IH), 2.69 (dt, J = thiadiazole-5-carboxamide 19.2, 7.1 Hz, IH), 2.59 (s, 3H), 1.02 (t, J = 7.3 Hz, 3H)
232 N-(4'-(N-(cyclopropylmethyl)-S- 1H-NMR (400 MHz, DMSO-d6) δ 10.46 (s, IH), 7.88 methylsulfonimidoyl)-[ 1,1'- (d, J = 8.7 Hz, 2H), 7.62 (d, J = 8.2 Hz, 2H), 7.46-7.55 biphenyl]-2-yl)-4-methyl- 1 ,2,3- (m, 4H), 3.15 (d, J = 6.4 Hz, 3H), 2.66-2.71 (m, IH), thiadiazole-5-carboxamide 2.59 (d, J = 4.1 Hz, 3H), 2.55 (t, J = 6.4 Hz, IH), 1.23
(s, IH), 0.82-0.85 (m, 2H), 0.28-0.33 (m, 2H)
233 (E)-N-(3-(N-cyano-S- Ή-NMR (400 MHz, DMSO- ) <·>' 11 -40 (s, I H), 8.18 isopropylsulfmimidoyl)phenyl)-4- (s, IH), 7.93 (d, 7 = 8.2 Hz, IH), 7.70 (t, J = 7.8 Hz, (difluoromethyi)- 1 ,2,3-thiadiazole-5- I H), 7.64 (t, 7 = 52.7 Hz, IH), 7.63 (d, 7 = 6.9 Hz, I H), carboxamide 3.59 (septet, 7 = 6.6 Hz, IH), 1.26 (d, 7 = 6.9 Hz. 3H),
1.12 (d, 7 = 6.4 Hz, 3H).
234 N-(4-(N-cyanopropan-2- ' H-NMR (400 MHz, OMSO-d6) δ 11.48 (s, IH), 8.34 yl.sulfonimidoyl.)phenyl)-4- (t, 7 = 1.8 Hz, IH), 8.15-8.04 (m, IH), 7.83 (t, 7 = 7.8 (difluoromethyl)- 1 ,2,3-thiadiazole-5- Hz, IH), 7.81-7.75 (m, IH), 7.64 (t, 7 = 52.7 Hz, I H), carboxamide 3.98 (septet, 7 = 6.6 Hz, IH), 1.33 (d, 7 = 6.9 Hz, 3H), 1.21 (d, 7 = 6.9 Hz, 3H).
235 N-cy clohexyl -4 - (difl u orometh yl) - Ή-NMR (400 MHz, OMSQ-d6) δ 9.00 (d, J = 7.5 Hz, 1,2, 3 -thiadiazole- 5 - c ar boxamide I H), 7.55 (t, J = 53.0 Hz, I H), 3.73 (q, J = 3.6 Hz, I H),
1.84 (d, ./ = 9.6 Hz, 2H), 1.69-1 :72 (m, 2H), 1.57 (d, ./ = 12.7 Hz, IH), 1.10-1.31 (m, 5H).
236 N-cyclohexyl-4-(diiluoromethyl)- Ή-NMR (400 MHz, OMSO-d6) δ 10.92 (d, J = 6.4 1,2, 3 - thiadiazole- 5 -c arbo thioamide Hz, I H), 7.46 (t, j = 52.9 Hz, IH), 4.29 (t, J = 3.7 Hz,
IH), 1.97-2.00 (m, 2H), 1.72-1.75 (m, 2H), 1.60 (d, J = 12.1 Hz, IH), 1.29-1.37 (m, 4H), 1.16-1.20 (m, I H); LCMS (M-l): 275.85
237 4-(difluoromethyl)-N-isopropyl- Ή-NMR (400 MHz, OMSO-d6) S 9.01 (d, J = 6.4 1 ,2,3-thiadiazole-5-carboxamide Hz, IH), 7.56 (t, J = 53.0 Hz, IH), 4.04 (m, / = 14.0,
6.6 Hz, IH), 1 .15 (d, J = 6.6 Hz, 6H); LCMS (M-l ): 219.90
238 4-(difluoromethyl)-N-isopropyl- Ή-NMR (400 MHz, DMSO- ) S 10.96 (s, IH), 7.47
1,2, 3 - thiadiazole- 5 -c arbo thioamide (t, / = 52.8 Hz, IH), 4.55 (m, J = 14.1, 6.7 Hz, IH),
1.24 (d, J = 6.6 Hz, 6H): LCMS (M-l): 235.85
239 (4-(diiluoromethyl)- 1 ,2,3 -thiadiazol- IH-NMR (400 MHz, DM Si )-.'/,,) δ 7.59 (t, ./ = 53.0 5-yl)(morpholino)methanone Hz, I H), 3.64 (d, J = 5.5 Hz, 4H), 3.51 (t, ./ = 4.7 Hz,
2H), 3.16 (t, J = 4.7 Hz, 2H), LCMS (M+l): 250.10
240 (4-(diiluoromethyl)- 1 ,2,3 -thiadiazol- IH-NMR (400 MHz, DMSO- ) δ 7.59 (t, / = 52.9 5-yl)(morpholino)methanethione Hz, IH), 3.87 (t, J = 5.0 Hz, 2H), 3.40 (t, J = 5.0 Hz,
2H), 2.70 (t, J = 5.0 Hz, 2H), 2.54-2.56 (m, 2H), LCMS (M+l) 266.00
241 (4-(difluoromethyl)-l,2,3-thiadiazol- IH-NMR (400 MHz, DM SO -- /,,) δ 7.50 (t, J == 52,7 Hz, 5-yl)(thiomorpholino)methanone IH), 4.24-4.26 (m, 2H), 3.78 (t, J = 5.0 Hz, 2H),
3.56-3.59 (m, 2H), 3.47-3.49 (m, 2H), LCMS (M+l): 266.00
242 (4-(difluoromethyl)- 1 ,2,3 -thiadiazol- I H-NMR (400 MHz, DMSO-<¾) δ 7.49 ft, ./ = 52.6 5 -yl) (thi omorphoii no )meth anethione Hz, IH), 4,52 (q, ./ - 3.4 Hz, 2H), 3.73 (t, .,/ - 5.2 Hz,
2H), 2.86-2.88 (m, 2H), 2.66 (t, J = 1 .8 Hz, 2H), LCMS (M): 281.00
243 (4-(difluoromethy 1.)- 1 ,2,3 -thiadiazol- Ή-NMR (400 MHz, DMSO-tfc) δ 7.58 (t, J = 53.0 Hz, 5-yl)(4-methylpiperazin- 1 - IH), 3.62 (t, J = 4.8 Hz, 2H), 3.14 (t, J = 5.0 Hz, 2H), yl)methanone 2.38 (t, ./ 4.8 Hz, 2H), 2.25 (t, ./ - 4.7 Hz, 2H), 2.18
(d, J = 6.0 Hz, 3H)
244 4-(chloromethyl)-N-(4-(pentafluoro- 'H-NMR (400 MHz, DMSO- ) δ 11.28 (s, IH), 16-sulfaneyl)phenyl)- 1 ,2,3- 7.96-7.88 (m, 4H), 5.30 (s, 2H); LCMS (M-2): 377.80 thiadiazole-5-carboxamide
245 4-(chloromethyl)-N-(3-(pentafluoro- Ή-NMR (400 MHz, DMSO- ) ' H -22 (s, I H), 8.32 16-sulfaneyl)phenyl)- 1 ,2,3- (s, IH), 7.92 (d, IH), 7.73-7.63 (m, 2H),5.31 (s, 2H); thiadiazole-5-carboxamide LCMS (M-2): 377.70
246 N-(3',4'-dichloro-5-ilu.oro-[l, r- {H-NMR (400 MHz, CDC13) δ 8.16 (dd. ./ = 9.2, 5.2 biphenyl]-2-yl)-4-(difluoromethyl)- Hz, IH), 7.91 (broad singlet, IH), (t, ./ = 2.1 Hz, IH), 1 ,2, 3 -thi adiazo 1 e- 5 -c arboxaniide 7.56-7.51 (m, IH), 7.47-7.45 (m, I H), 7.44 (t, ,/ = 52.6
Hz, IH), 7.20-7.15 (m, IH), 7.02 (dd, J = 8.8, 3.2 Hz, IH)
247 N-(3',4'-dichloro-5-fluoro-[l, l'- ' H-NMR (400 MHz, DMSO--4 δ 12.45 (s, I H), 7.74 biphenyl.]-2-yl)-4-(difluoromethyl)- (d, J = 8.3 Hz, IH), 7.61-7.67 (m, 2H), 7.23-7.50 (m, l,2,3-thiadiazole-5-carbothioamide 4j 15: LCMS (M-i): 431.75 248 4-(dffluoromethyl)-N-(3',4',5'- 1H-NMR (400 MHz, CDC13) δ 8.25 (d, ,/ = 8.4 Hz, trifluoio - [ 1 , 1 '-biphenyl] -2-yl)- 1 ,2,3- IH), 8.01 (broad singlet, I H), 7.51-7.46 (rn, I H), thiadiazole-5-carboxamide 7.35-7.28 (m, 2H), 7.31 (t, / = 52.6 Hz, I H), 6.99 (m,
2H)
249 4-(difluoromethyl)-N-(3',4',5'- 1H-NMR (400 MHz, DMSO-i¾ δ 12.48 (s, IH), trifluoro - [1,1 '-biphenyl] -2-yl) - 1 ,2,3 - 7.28-7.57 (m, 7H); LCMS (M-l): 399.85
thiadiazole-5-carbothioamide
250 4-(difluoromethyl)-N-methoxy-N-( l- Ή-NMR (400 MHz, DMSO-i¾) S 7.43-7.69 (m, 3H), (2,4,6-trichlorophenyl)propan-2-yl)- 4.80 (d, J = 6.4 Hz, I H), 3.77 (s, 3H), 3.34-3.40 (m, 1,2,3 - thiadiazole- 5 -c arboxamide IH), 3.19-3.24 (m, IH), 1.43 (d, J = 6.9 Hz, 3H);
LCMS (M+l): 429.95
251 N-(3\4'-dicWoro-5-fluoro-[l, l'- 1H-NMR (400 MHz, CDC13) δ 8.16 (s, I H), 7.59 (d, J biphenyl.]-2-yl)-4-isopropyl- 1,2,3- = 8.5 Hz, IH), 7.49 (d, J = 1.8 Hz, IH), 7.15-7.22 (m, thiadiazole-5-carboxamide 2H), 7.03 (dd, J = 8.5, 3.1 Hz, I H), 3.39-3.50 (m, IH),
1.41 (d, 7 = 7.3 Hz, 6H)
252 4-isopropyl-N-(3',4',5'-(rifluoro-[ l, - 1 H-NMR (400 MHz, CDCi3) δ 8. 1 (d, ,/ - 7.8 Hz, biphenyl] -2-yl)- 1 ,2,3 - thiadiazole- 5- IH), 7.47-7.51 (m, IH), 7.27-7.35 (m, 3H), 7.07-7.07 carboxamide (OH), 7.03 (dt, J = 13.3, 6.1 Hz, I H), 3.50-3.57 (m,
IH), 1.57 (s, 2H), 1.44 (d, J = 6.9 Hz, 5H)
253 N-(2-(3-chloro-5- 1H-NMR (400 MHz, CDCi3) δ 8.70 (s, IH), 7.96 (d, J
(trifluoromethyl)pyridin-2-yl)ethyl)- = 1.4 Hz, IH), 7.02 (d, ,/ = 17.9 Hz, IH), 3.98 (q, ,/ = 4-isopropyl- 1 ,2,3 -thiadiazole-5- 5.8 Hz, 2H), 3.60-3.67 (m, IH), 3.32 (t, / = 5.5 Hz, carboxamide 2H), 1.63 (s, 4H), 1.45-1.50 (rn, 6H)
254 N-(4'-chloro- [1,1 '-biphenyl] -2-yl)-4- 1H-NMR (400 MHz, 1 )MS( ) ·· /,, } δ 10.39 (s, I H), methyl- 1 ,2,3-thiadiazole-5- 7.42-7.53 (in, 9H), 2.61-2.69 (m, 3H)
carboxamide
255 N-(3\4'-dichloro-5-fluoro-[l, l'- ' H-NMR (400 MHz, CDC13) δ 8.19 (broad singlet, biphenyl.]-2-yl)-4-methyl- 1 ,2,3- IH), 7.59 (d, J = 8 Hz, IH), 7.50 (broad s, IH), 7.34 (s, thiadiazole-5-carboxamide IH), 7.20 -7.15 (m, 2H), 7.01 ( dd, ,/ = 8.4, 2.8 Hz)
2.71 (s, 3H)
256 4-methyl-N-(3,,4',5'-trifluoro-[ 1 , 1 '- 1 H-NMR (400 MHz, CDC13) δ 7.91 (broad singlet, biphenyl] -2-yl)- 1,2,3 -thiadiazole- 5- IH), 7.51-7.46 (rn, IH), 7.40 (broad s, I H), 7.34-7.27 carboxamide (m, 2H), 7.07-6.99 (m, 2H), 2.81 (s, 3H)
257 N-(4'-chloro- [ 1 , 1 '-biphenyl] -2-yl)-4- 1. H-NMR (400 MHz, DMSO-d6) δ 10.67 (s, I H), 7.58 (difluoromethyl)- 1 ,2,3-thiadiazoIe-5- (d, J = 7.8 Hz, IH), 7.38-7.51 (m, 7H),
carboxamide
258 4-(difluoromethyl)-N-(2-(4- 1 H-NMR (400 MHz, DMSO-^) δ 10.68 (s, IH), methylpentan-2-yl)phenyl)- 1 ,2,3- 7.30-7.38 (m, 3H), 7.24 (td, J = 7.5, 1.4 Hz, IH), 3.05 thiadiazole-5-carboxamide (td, J = 13.6, 6.7 Hz, IH), 1.29-1.47 (m, 4H), 1.13 (d, ./
= 7.3 Hz, 3H), 0.79 (dd, J = 9.8, 6.1 Hz, 6H)
259 4-(difluoromethyl)-N-(3- 1 H-NMR (400 MHz, DMSO-tfc) δ 1 1.033 (s, IH), (isopropylthio)phenyl)- 1 ,2,3- 7.35-7.50 (m, 3H), 7.63-7.73 (m, 2H); 3.3(s, I H), thiadiazole-5-carboxamide 1.25-1.27 (d, 6H),; LCMS (M-l): 327.8
260 4-(difluoromethyl)-N-(3- 1 H-NMR (400 MHz, OMSO-d6) δ 1 1 .27 (s, I H), (isopropylsulfinyl)phenyl)- 1 ,2,3 - 7.39-7.60 (m, 3H), 7.64-7.97 (m, 2H); 2.92-2.94(m, thiadiazole-5-carboxamide 1H), 1.19-1.23 (m, 3H) 0.93-0.95(d,3H); LCMS
(M+l): 345.8
261 4-(difluoromethyl)-N-(3- 1H-NMR (400 MHz, DMSO-ii6) δ 11.36 (s, IH), (isopropylsulfonyl)phenyl)- 1 ,2,3- 7.50-7.68 (m, 3H), 7.70-8.50 (m, 2H); i .90-2.07(m, thiadiazole-5-carboxamide 1 H), 1 .15- 1.19 (m, 6H); LCMS (M-l): 359.9 262 4-(difluoromethyl)-N-(2-( 1 - 1H-NMR (400 MHz, DMSO-i¾s) δ 10.71 (s, IH),
(isopropylthio)ethyl)phenyl)- 1 ,2,3- 7.50-7.77 (m, 2H), 7.27-7.38 (m, 3H), 4.31 (q, J = 6.9 thiadiazole-5-carboxamide Hz, IH), 2.60-2.66 (m, I H), 1.45 (d, ./ = 6.9 Hz, M i ).
1.11 (d, J = 6.6 Hz, 3H), 1.03 (d, J = 6.7 Hz, 3H); LCMS (M-l ): 355.90
263 4-(difluoromethyl)-N-(2-( 1 - Ή-NMR (400 MHz, DMSO-i ) δ 12.40 (s, I H),
(isopropylthio)ethyl)phenyl)- 1 ,2,3- 7.53-7.80 (m, 2H), 7.33-7.41 (m, 3H), 4.21 (q, J = 7.0 thiadiazole-5-carbothioamide Hz, IH), 2.68-2.75 (m, IH), 1.43 (dd, J - 13.3, 7.0 Hz,
3H), 1.15 (d, / = 6.7 Hz, 3H), 1.05 (d, ,/ = 6.7 Hz, 3H); LCMS (M-l): 371.90
264 4-methyl-N-(4-(pentafluoro-16- 1H-NMR (400 MHz, DMSO- ) S 12.56 (s, IH),
sulfaneyl)phenyl)- 1 ,2,3-thiadiazole- 7.96-8.11 (m, 4H), 2.64-2.73 (s, 3H); LCMS (M-l):
5-carbothioaniide 360.3
265 N-(3-chloro-4-methylphenyl)-4- Ή-NMR (400 MHz, DMSO-i¾) δ 12.27 (s, I H), 8.00 met yl- 1 ,2,3-thiadiazole-5- (d, J - 1.8 Hz, IH), 7.56-7.63 (m, IH), 7.42 (d, / = 8.3 carbothioamide Hz, IH), 2.75 (s, 3H), 2.33 (s, 3H); LCM S (M-l ):
281.85
266 4-methyl-N-(m-i.olyl)- 1 ,2,3- 'H-NMR (400 MHz, DMSO-i¾) S 12.22 (s, IH), 7.60 thiadiazole-5-carbothioamide (d, ./ - 7.9 Hz, 2H), 7.34 (t, ./ = 7.6 Hz, 1 H), 7.14 (d, ./ =
7.5 Hz, IH), 2.72 (s, 3H), 2.32 (s, 3H); LCMS (M-l): 248.3
267 N-(3-isopropoxyphenyl)-4-methyl- Ή-NMR (400 MHz, DMSO- δ 12.23 (s, I H), 7.59 l,2,3-thiadiazole-5-carbothioamide (d, J = 1.8 Hz, IH), 7.30-7.36" (m, 2H), 5.85-6.88 (m,
IH), 4.55-4.61 (rn, I H), 2.72 (s, 3H), 1.23-1.30 (m, 6H); LCMS (M-l ): 291.9
268 4-methyl-N-phenyl- 1 ,2,3 - Ή-NMR-NMR (400 MHz, DMSO- ') δ 12.28 (s, thiadiazole-5-carbothioamide IH), 7.83 (dd, / = 8.6, 0.9 Hz, 2H), 7.45-7.48 (m, 2H),
7.32 (i, / = 7.4 Hz, IH), 2.74 (s, 3H): LCMS (M- l): 234.32
269 N-(2-chloro-4- 1H-NMR (400 MHz, OMSO-d6) δ 11.13 (s, I H), 8.10
(methylsulfonyl)phenyl)-4- (d, J = 2.1 Hz, I H), 8.08 (d, J = 8.4 Hz, IH), 7.97 (dd, J
(difluoromethyl)- 1 ,2,3-thiadiazole-5- = 8.6, 2.1 Hz, I H), 7.63 (t, ./ = 53.0 Hz, IH), 3.30 (s, carboxamide 3H); LCMS (M-l): 365.80
270 N-(2,6-dichlorophenyl)-4- 1H-NMR (400 MHz, DMSO-i¾ δ 11.30 (s, IH), (difluoromethyl)- 1 ,2,3-thiadiazole-5- 7.44-7.75 (m, 4H); LCMS (M-l): 321.75
carboxamide
271 N-(4'-chloro- [ 1 , l'-biphenyl] -3 -yl)-4- Ή-NMR (400 MHz, D. Si)-,-/,. ) δ 1 1.13 (s, IH), 7.99
(difluoromethyl)- 1 ,2,3-thiadiazole-5- (s, IH), 7.49-7.78 (m, 8H); LCMS (M-l): 363.85 carboxamide
272 N-([ 1 , 1 '-biphenyl] - 3-yl)-4- {H-NMR (400 MHz, Ethanol-J5) δ 11.07 (s, IH), 7.95
(difluoromethyl)- 1 ,2,3 -thiadiazole- 5 - (s, IH), 7.75-7.36 (ni, 9H); LCMS (M-l): 329.85 carboxamide
273 N-(3',4'-difluoro-[l , 1 '-biphenyl]-3- Ή-NMR (400 MHz, DMSO- 6) δ 1 1.20-11.02 (bs. yl)-4-(difluoromethyl) - 1 ,2,3- * IH), 7.95 is, IH), 7.83-7.35 (m, 7H); LCMS (M-l ): thiadiazole-5-carboxamide 365.85
274 4-(difluoromethyl)-N-(3',4',5'- Ή-NMR (400 MHz, OMSO~d6) δ 11.14 (s, IH), 7.96 trifluoro- [1,1 '-biphenyl] -3-yl)- 1 ,2,3- (s, I H), 7.49-7.78 (m, 6H); LCMS (M-l): 383.85 thiadiazole-5-carboxamide
275 4-(difluoromethyl)-N-(3',4'- Ή-NMR (400 MHz, DMSO- ') δ 11.07 (s, I H), 7.92 dimettiyl- [ 1 , 1 '-biphenyl] -3-yl)- 1,2,3- (s, I H), 7.77-7.21 (m, 7H), 2.28 (d, 6H); LCMS (M-l): thiadiazole-5-carboxamide 357.90 276 N-(4-(difluoromethoxy)phenyl)-4- 1H-NMR (400 MHz, DMSO-rfi) δ 7.59 (s, IH), (difluoromethyl)-N-methyl- 1 ,2,3- 7.46-7.48 (m, 2H), 7.36 (d, 7 = 31.8 Hz, IH), thiadiazole-5-carbothioaniide 7.04-7.22 (m, 2H), 3.81 (s, 3H); LCM S (M+ l): 352.05
277 4-(difluoromethyl)-N-(2- Ή-NMR (400 MHz, OM$0~d6) δ 11.25 (s, IH), 7.84 ((lrifluoromethyl)thio)phenyl)- 1 ,2,3- (d, ,/ = 7.9 Hz, I H), 7.47-7.74 (m, 4H); LCMS M-l): thiadiazole-5-carboxamide 353.80
278 4-(difluoromethyl)-N-(2- Ή-NMR (400 MHz, D. SO-, ,, ) δ 13.04(s, IH), 7.87 ((lrifluoromethyl)thio)phenyl)- 1 ,2,3- (d, J = 7.6 Hz, I H), 7.45-7.75 (m, 4H); LCMS (M-l): thiadiazole-5-carbothioamide 369.80
279 N-(4-bromo-2- 1H-NMR (400 MHz, OMSO-de) δ 11.27 (s, IH), 8.03
((trifluoromethyl)thio)phenyl)-4- (d, / = 1.8 Hz, I H), 7.92 (dd, / = 8.6, 2.3 Hz, I H), (difkioromethyl)- 1 ,2,3-thiadiazole-5- 7.47-7.74 (m, 2H); LCMS M-l): 433.70
carboxamide
280 N-(2,4-dibromo-6- 1H-NMR (400 MHz, DMSO-dtf) δ 11.60 (s, IH), 8.36 ((trifluoromethyl)thio)phenyl)-4- (s, IH), 8.14 (s, IH), 7.60 (t, IH); LCMS (M- l): (difkioromethyl)- 1 ,2,3-thiadiazole-5- 51 1.65
carboxamide
281 N-(4-chloro-2- 1H-NMR (400 MHz, DMSO-d6) δ 1 1.27 (s, IH), 7.92
((trifluoromethyl)thio)phenyl)-4- (s, IH), 7.81 (d, I H), 7.73-7.46 (m, 2H): LCMS (M-2): (difkioromethyl)- 1 ,2,3-thiadiazole-5- 387.75
carboxamide
282 N-(2,4-dichloro-6- Ή-NMR (400 MHz, DMSO--4 δ 1 1.61 (s, I H), 8.15 ((trifluoromethyl)thio)phenyl)-4- (s, IH), 8.01 (s, IH), 7.61 (i, IH); LCMS (M-2): (dif uoromethyl)- l,2,3-thiadiazole-5- 421.75
carboxamide
283 N-(2-chloro-4- Ή-NMR (400 MHz, DMSO- ) δ 1 1.24 (s, I H), 8.41
((trifluoromethyl)sulfonyl)phenyl)-4- (d, / = 8.7 Hz, IH), 8.32 (d, 7 = 2.1 Hz, IH), 8.22 (dd, J (dif uoromethyl)- l,2,3-thiadiazole-5- = 8.7, 2.1 Hz, IH), 7.66 (t, J - 52.9 Hz, IH); LCMS carboxamide (M-l): 419.80
284 4-(difluoromethyl)-N-(4- Ή-NMR (400 MHz, DMSO- ) δ 11.65 (s, IH), 8.17
((triflu oromethyl) sulf ony l)phenyl) - (d, J = 8.9 Hz, 2H), 8.08 (dd, / = 7.1, 1.9 Hz, 2H), 7.63 l,2,3-thiadiazole-5-carboxamide (t, 7 = 52.7 Hz, IH); LCMS(M-l) 385.80
285 4-(difluoromethyl)-N-(3- Ή-NMR (400 MHz, DMSO-i/6) δ 12.79 (s, IH), 8.32
((trifluoromethyl)sulfinyl)phenyl)- (s, I H), 8.01 (d, 7 = 7.5 Hz, IH), 7.49-7.75 (m, 3H); l,2,3-thiadiazole-5-carbothioamide LCMS (M- l): 387.3
286 4-(difluoromethyl)-N-(3- Ή-NMR (400 MHz, DMSO-rf6) δ 12.94 (s, IH), 8.91 nitrophenyl)-l,2,3-thiadiazole-5- (t, 7 = 2.0 Hz, I H), 8.17-8.21 (m, 2H), 7.50-7.80 (m, carbothioamide 2H); LCMS (M-l): 314.8
287 4-(difluoromethyl)-N-(2- 1H-NMR (400 MHz, DMSO- ) δ 12.95 (s, IH), 8.14 nitrophenyl)- 1 ,2,3-thiadiazole-5- (d, 7 = 8.1 Hz, IH), 7.87 (t, 7 = 7.6 Hz, I H), 7.45-7.71 carbothioamide (m, 3H); LCMS (M-l ): 314.8
288 N-(2-bromo-5- Ή-NMR (400 MHz, DMSO- δ 12.79 (s, I H), 8.04
((trifluoromethyl)thio)phenyl)-4- (d, J = 1.7 Hz, IH), 7.94 (d, 7 = 8.4 Hz, IH), 7.62-7.83 (difluoromethyl)- 1 ,2,3-thiadiazole-5- (m, 2H); LCMS (M-l ): 449.01
carbothioamide
289 N-(2-bromo-4- Ή-NMR (400 MHz, DMSO--4 δ 12.94 (s, I H), 8.10
((trifluoromethyl)thio)phenyl)-4- (s, IH), 7.88-7.73 (m, 3H), 7.67-7.48 (m, 3H); LCMS
(dif uoromethyl)- l,2,3-thiadiazole-5- (M-l): 449.1
carbothioamide 290 4-(difluoromethyl)-N-(4- 1H-NMR (400 MHz, OMSO-d6) δ 12.81 (s, I H), 8.05
( ( trifluoromethy 1) sulfinyl)phenyl) - (d, ./ = 8.4 Hz, 2H), 7.83 (d, J = 8.6 Hz, 2H), 7.61 (t, / = l,2,3-thiadiazole-5-carbothioamide 52.6 Hz, IH); LCMS (M-l): 387.3
291 4-(difluoromethyl)-N-(3- 'H-NMR (400 MHz, OMSO-d6) δ 13.18-12.76 (IH),
( ( trifluoromethy 1) sulfonyl)phen yl) - 8.77 (s, IH), 7.90-8.27 (m, 3H), 7.63 (s, IH); LCMS
1,2,3 -thiadiazole-5 -carbothioamide (M-l): 402.3
292 4-(difluoromethyl)-N-(4- Ή-NMR (400 MHz, 1 )MS( ) ·· /,, } δ 13.10 (s, IH),
(( trifluoromethy l)sulfonyl)phen yl)- 8.22-8.37 (m, 4H), 7.65 (t, ./ = 52.5 Hz, IH); LCMS l,2,3-thiadiazole-5 -carbothioamide (M-l): 401.8
293 N-(2,6-dibromo-4- Ή-NMR (400 MHz, DMSO-4) δ 11.56 (s, I H), 8.20 ((trifluoromethyl)thio)phenyl)-4- (s, 2H), 7.62 (t, J = 52.9 Hz, I H); LCMS (M-l): 511.75 (difluoromethyl)- 1 ,2,3-thiadiazole-5- carboxamide
294 N-(3-(pentafluoro-16- Ή-NMR (400 MHz, CDC13) δ 8.01 (d, J = 8.2 Hz, sulfaneyl)phenyl)-4- I H), 7.93 (d, ./ = 16.5 Hz, I H), 7.81 (d, 7 = 7.9 Hz, I H),
(((trifl uorometh yl)thio)methy 1 )- 7.64 (d, J = 8.3 Hz, I H), 7.53 (t, J = 8.0 Hz, I H), 4.84 l,2,3-thiadiazole-5-carboxamide (s, 2H)
295 N - (4 - (pentafluoro -16- Ή-NMR (400 MHz, CDC13) δ 7.89 (s, I H), 7.79-7.82 sulfaneyl)phenyl)-4- (m, 2H), 7.71 (d, J = 8.9 Hz, 2H), 4.84 (s, 2H)
(((trifluoromethyl)thio)methyl)- l,2,3-thiadiazole-5-carboxamide
296 4-(difluoromethyl)-N-(4- Ή-NMR (400 MHz, DMSO-J6) δ 10.72 (s, I H), (dimethylamino)phenyl)- 1 ,2,3- 7.46-7.74 (3H), 6.72 (dd, / = 7.0, 2.1 Hz, 2H), 2.87 (s, thiadiazole-5-carbox amide 6H); LCMS (M-l): 296.9
297 4-(difluoromethyl)-N-(4- ¾-NMR (400 MHz, DMSO- ) δ 12.36 (s, IH), 7.75 (dimethylamino)phenyl)- 1 ,2,3- (d, ,/ = 9.0 Hz, 2H), 7.56 (t, / = 52.7 Hz, I H), 6.75 (d, / thiadiazole-5-carbothioamide = 9.2 Hz, 2H), 2.93 (s, 6H); LCMS (M-l): 312.85
298 N-(4-(tert-butyl)phenyl)-4- Ή-NMR (400 MHz, DMSO- ) δ 10.94 (s, IH), (difluoromethyl)- 1 ,2,3-thiadiazole-5- 7.48-7.75 (m, 3H), 7.40 (d, J = 8.7 Hz, 2H), 1.27 (s, carbox amide 9H); LCMS (M-l ): 309.9
299 N-(4-(tert-butyl)phenyl)-4- Ή-NMR (400 MHz, DMSO-rf6) δ 12.54 (s, IH), 7.78 (difluoromethyl)- 1 ,2,3-thiadiazole-5- (d, ./ = 8.7 Hz, 2H), 7.44-7.71 (m, 3H), 1.29 (s, 9H); carbothioamide LCMS (M-l): 324.95
300 N-(2-bromo-4- 1H-NMR (400 MHz, DMSO- ) δ 11.10 (s, IH), 8.21
((trifluoromethyl)sulfinyl)phenyl)-4- (d, J = 1.5 Hz, IH), 8.05 (d, J - 8.6 Hz, IH), 7.99 (dd, ./ (difluoromethyl)- 1 ,2,3 -thiadiazole-S- = 8.5, 1.5 Hz, I H), 7.64 (t, ,/ = 52.8 Hz, IH); LCMS carboxamide (M-l): 449.1
301 N-(4-chloro-2- Ή-NMR (400 MHz, OMSO-d6) δ 13.03 (s, I H),
((trifluoromethyl)thio)phenyl)-4- 7.50-7.94 (m, 4H); LCMS (M-2): 403.80
(difluoromethyl)- 1 ,2,3-thiadiazole-5- carbothioamide
302 4-(difluoromethyl)-N-(2- 1 H-NMR (400 MHz, DMSO-d6) δ 1 1.35 (s, IH), 8.00
((tri f 1 uorometh yl) su 1 fin yl )phen yl ) - (d, J - 7.8 Hz, IH), 7.82-7.86 (m, I H), 7.50-7.76 (m, l,2,3-thiadiazole-5-carboxamide 3! 15: LCMS (M-l): 369.75
303 4-(difluoromethyl)-N-(4- 1H-NMR (400 MHz, DMSO-d6) δ 1 1.20 (s, IH), ((difluoromethyl)thio)phenyl)- 1 ,2,3- 7.30-7.76 (m, 6H); LCMS (M-l ): 335.75
thiadiazole-5-carboxamide
304 N-(4-bromo-2- 1 H-NMR (400 MHz, DMSO-d6) δ 1 1.38 (s, IH),
((trifluoromethyl)sulfinyl)phenyl)-4- 8.00-8.07 (m, 2H), 7.50-7.76 (m, 2H); LCMS (M+l): (difluoromethyl)- 1 ,2,3-thiadiazole-5- 449.65
carboxamide 305 4-(difluoromethyl)-N-(4- 1H-NMR (400 MHz, DMSO-di) δ 12.74 (s, IH), 7.97 ((difluoromethyl)thio)phenyl)- 1 ,2,3- (d, 7 = 7.9 Hz, 2H), 7.37-7.73 (m, 4H); LCMS ( M- 1 ): thiadiazole-5-carbothioaniide 351.75
306 N-(4-bromo-2- 1H-NMR (400 MHz, DMSO-d6) δ 13.02 (s, I H), 8.05
((trifluoromethyl)thio)phenyl)-4- (s, IH), 7.94 (d, J = 6.7 Hz, IH), 7.50-7.76 (m, 2H); (difluoromethyl)- 1 ,2,3-thiadiazole-5- LCMS (M+0): 449.65
carbothioamide
307 N-(2-chloro-4-(pentafluoro-16- 1H-NMR (400 MHz, DMSO-d6) δ 1 1.07 (s, IH), 8.21 sulfaneyl)phenyl)-4-(chloromethyl)- (d, J = 2.3 Hz, IH), 7.97-8.03 (m, 2H), 5.32 (s, 2H); l,2,3-thiadiazole-5-carboxaniide LCMS (M-2): 41 1 .80
308 N-(4 -bromophenyl )-4- ΊΙ- MR (400 MHz, OM$0~d6) δ 12.66 (s, IH), 7.81 (difluoromethyl)- 1 ,2,3-thiadiazole-5- (d, J = 8.6 Hz, 2H), 7.47-7.74 (m, 3H); LCMS (M-l): carbothioamide 349.70
309 4-(difluoromethyl)-N-(2,4,6- 1H-NMR (400 MHz, DMSO-i¾ S 13.12 (s, IH), tribromophenyl)- 1 ,2,3-thiadiazole-5- 8.06-8.21 (m, 2H), 7.47-7.76 (m, IH); LCMS (M- l): carbothioamide 507.60
310 N-(3,5-dichlorophenyl)-4- 1H-NMR (400 MHz, DMSO-4) δ 12.80 (s, I H), 7.93 (difkioromethyl)- 1 ,2,3-thiadiazole-5- (d, J = 1.2 Hz, 2H), 7.48-7.74 (m, 2H); LCMS (M-l): carbothioamide 337.75
311 N-(2-cyanophenyl)-4- Ή-NMR (400 MHz, DMSO-i¾) «512.66 (s, IH), 8.69 (difkioromethyl)- 1 ,2,3-thiadiazole-5- (dd, J = 8.3, 1.4 Hz, IH), 8.11-8.15 (m, 2H), 8.01 (dd, carbothioamide / = 8.1, 1.2 Hz, I H), 7.82-7.86 (m, I H); LCMS (M-l ):
295.3
312 N-(2,5-dichlorophenyl)-4- Ή-NMR (400 MHz, OM$0-d6) δ 12.70 (d, J = 26.7 (difluoromethyl)- 1 ,2,3-thiadiazole-5- Hz, IH), 7.48-7.84 (m, 4H); LCMS (M-l ): 337.75 carbothioamide
313 N-(2,6-dichlorophenyl)-4- Ή-NMR (400 MHz, DMSO-i ) δ 12.79-12.85 (s,
(dif uoromethyl)- l,2,3-thiadiazole-5- IH), 7.56-7.72 (m, 3H), 7.45 id. ./ - 8.0 Hz, IH); carbothioamide LCMS (M-l): 337.75
314 4- (difluoromethyl)-N- 'H-NMR (400 MHz, OMSO-de) δ 11.78 (s, IH), 7.60 (perbromophenyl)- 1 ,2,3 -thiadiazole- (t, / = 52.8 Hz, IH); LCMS (M-l): 647.45
5- carboxamide
315 N-(2,6-dibromo-4-nitrophenyl)-4- Ή-NMR (400 MHz, DMSO- ) 11.71 (s, I H), 8.60
(dif uoromethyl)- l,2,3-thiadiazole-5- (s, 2H), 7.63 (t, / = 52.8 Hz, IH); LCMS (M-l ): 456.70 carboxamide
316 N-(3,5-dibromophenyl)-4- Ή-NMR (400 MHz, OMSO-d6) δ 11.24 (s, I H), 7.88 (difkioromethyl)- 1 ,2,3-thiadiazole-5- (s, 2H), 7.49-7.75 (m, 2H); LCMS (M-l): 411.65 carboxamide
317 4-(difluoromethyl)-N-(2,3,4- 1H-NMR (400 MHz, DMSO-dtf) δ 11.08 (s, IH), 7.90 tribromophenyl)- 1 ,2,3-thiadiazole-5- (d, J = 8.6 Hz, I H), 7.48-7.74 (m, 2H); LCMS (M-l): carboxamide 489.60
318 N-(3,4-dibromophenyl)-4- Ή-NMR (400 MHz, DMSO-4) δ 11.21 (s, I H), 8.15 (difluoromethyl)- 1 ,2,3-thiadiazole-5- (d, / = 2.0 Hz, I H), 7.77 (d, / = 8.7 Hz, I H), 7.49-7.75 carboxamide (m, 2H); LCMS (M-l ): 411.65
319 N-(2,5-dibromophenyl)-4- Ί-1-NMR (400 MHz, DMSO- δ 10.99 (s, I H), 7.93 (difl.uoromethyl)- 1 ,2,3-thiadiazole-5- (s, I H), 7.46-7.75 (m, 3H); LCMS (M-l): 411.65 carboxamide
320 N-(3,4-dibromophenyl)-4- Ή-NMR (400 MHz, DMSO-4) δ 12.74 (s, I H), 8.37 (difkioromethyl)- 1 ,2,3-thiadiazole-5- (d, 7 = 2.3 Hz, I H), 7.87 (d, 7 = 8.6 Hz, I H), 7.47-7.73 carbothioamide (m, 2H); LCMS (M-l ): 427.60 321 N-(3,5-dibromophenyl)-4- 1H-NMR (400 MHz, OMSO-d6) δ 12.76 (s, IH), 8.07
(difluoromethyl)- l,2,3-thiadiazoIe-5- (s, 2H), 7.82 (s, IH), 7.60 (t, ./ = 52.3 Hz, IH); LCMS carbothioamide (M-l): 427.70
322 N-(2,5-dibromophenyl)-4- 'H-NMR (400 MHz, DMSO-di) δ 12.79 (s, IH), 7.89
(difluoromethyl)- l,2,3-thiadiazoIe-5- (d, / = 10.1 Hz, IH), 7.52-7.79 (m, 3H); LCMS (M-l): carbothioamide 427.70
323 N-(2,6-dibromo-4- Ή-NMR (400 MHz, I)MSO-d6) δ 11.63 (s, I H), 6.262
( trifluoromethy 1 )p heny 1 )-4- (s, 2H), 7.622 (t, / = 53.2 Hz, IH); LCMS(M-l): (difluoromethyl)- 1 ,2,3-thiadiazole-5- 479.75
carboxamide
324 N-(2-bromo-6-chloro-4- 1H-NMR (400 MHz, DMSO-rfd) δ 11.630 (s, I H), 8.26
( trifluoromethy 1 )p heny 1 )-4- (s, 2H), 7.62 (t, J - 52.9 Hz, IH). LCMS(M-l): 435.75 (difluoromethyl)- 1 ,2,3-thiadiazole-5- carboxamide
325 N-(2-bromo-6-fluoro-4- Ή-NMR (400 MHz, DMSO-rfi) δ 11.45 (s, IH), 8.09
( trifluoromethy 1 )p heny 1 )-4- (s, IH), 8.00 (d, J = 9.3 Hz, IH), 7.63 (t, J = 52.9 Hz, (difluoromethyl)- 1 ,2,3-thiadiazole-5- I H); LCMS(M--l ): 417.70
carboxamide
326 N-(3-chloro-5- 'H-NMR (400 MHz, DMSO-rfi) δ 11.93 (s, IH), 8.72
(( trifluoromethy] )thio)pyridin-2-y] .)- (d, J = 2.0 Hz, IH), 8.58 (d, J = 1.8 Hz, IH), 7.61 (t, J = 4 -(dill uorometh yl) - 1 ,2 , 3 -thi adiazole- 52.9 Hz, IH); LCMS(M- l): 388.75
5-carboxamide
N-(4-chloro-2- 'H-NMR (400 MHz, OMSO-d6) δ 11.07 (s, IH), 7.92
(trifluoromethoxy)phenyl)-4- (d, J = 8.7 Hz, IH), 7.48-7.77 (m, 3H); LCMS (M-l): (difluoromethyl)- 1 ,2,3-thiadiazole-5- 371.8
carboxamide
328 N-(4-chloro-2- Ή-NMR (400 MHz, DMSO-rfi) δ 12.66 (s, IH), 7.81
(trifluoromethoxy)phenyl)-4- (d, J = 8.7 Hz, IH), 7.44-7.72 (m, 3H); LCMS (M-l):
(difluoromethyl)- 1 ,2,3-thiadiazole-5- 387.7
carbothioamide
329 4-(difluoromethyl)-N-(2-methyl-4- Ή-NMR (400 MHz, DMSO-<¾j) δ 12.49 (s, IH),
(perfluoropropan-2-yl)phenyl)- 1 ,2,3- 7.53-7.80 (m, 4H), 2.35 (s, 3H); LCMS (M-l): 451.8 thiadiazole-5-carbothioamide
330 (4-(difluoroniethy ).)- 1 ,2,3 -thiadiazol- ¾-NMR (400 MHz, DMSO-tfc) δ 7.49-7.75 (ni, IH),
5-yl)(4-phenyl-3,6-di ydropyridin- 7.43 (d, ./ - 7.6 Hz, 2H), 7.35 (t, ./ = 7.5 Hz, 2H), 7.27
1 (2H) -yl)methanone (t, J - 7.2 Hz, IH), 6.22 -6.02 (m, IH), 4.30 (d, J - 1.8
Hz, 2H), 3.86 (d, ./ = 5.8 Hz, 2H), 3.40 (t, ./ = 5.7 Hz, IH), 2.59 (s, IH): LCMS (M-l): 320.3
331 N-(2,6-dibromo-4- Ή-NMR (400 MHz, DMSO-ifc) δ 11.46 (s, I H), 7.98
(trifluoromethoxy)phenyl)-4- (s, 2H), 7.64 ((, J = 53.0 Hz, I H); LCMS (M-l): 495.7 (difluoromethyl)- 1 ,2,3-thiadiazole-5- carboxamide
332 N-(2,4-dibromo-6- Ή- MR (400 MHz, DMSQ-i¾) δ 11.33 (s, IH), 8.16
(trifluoromethoxy)phenyl)-4- (s, I H), 7.87 (s, I H), 7.61 (t, / = 53.0 Hz, I H); LCMS (difluoromethyl)- 1 ,2,3-thiadiazole-5- (M-l): 495.7
carboxamide
333 N-(2,4-dibromo-6- 1H-NMR (400 MHz, DMSO-^) δ 12.85 (s, IH),
(trifluoromethoxy)phenyl)-4- 8.15-8.18 (m, I H), 7.86 (s, IH), 7.51-7.80 (m, IH);
(difluoromethyl)- 1 ,2,3-thiadiazole-5- LCMS (M-l): 511.7
carbothioamide
334 N-allyl-4-(difluoromethyl)- 1 ,2,3- 1H-NMR (400 MHz, DMSO-^) δ 9.36 (s, IH), 7.58 (t,
HQ thiadiazole-5-carbox amide J = 53.0 Hz, I H), 5.81-5.91 (m, I H), 5.22 (dt, J = 1 7.
1.6 Hz, I H), 5.13 (dt, ./ = 10.3, 1.5 Hz, I H), 3.90 (d, /
3.7 Hz, 2H); LCMS (M- l): 217.9
335 I 4-(difluoromethyl)-N-(prop-2-yn-l- -NMR (400 MHz, OMSO-d6) δ 9.65 (t, ,/ = 4.7 Hz, yl)-l,2,3-thiadiazole-5-carboxamide 7.54 (t, J = 53.0 Hz, IH), 4.05 (q, J = 2.6 Hz, 2H),
3.22 (t, J = 2.5 Hz, IH); LCMS (M-l ): 215.9
336 ! N-(2-bromo-6-methyl-4- Ή-NMR (400 MHz, DMSO- ) δ 11.17 (s, IH), 7.80
(perfluoropropan-2-yl)phenyl)-4- (s, IH), 7.48-7.75 (m, 2H), 2.37 (s, M i ): LCMS (M-l): (difluoromethyl)- 1 ,2,3-thiadiazole-5- 515.8
carboxamide
N-(2-chloio-4- Ή-NMR (400 MHz, OMSO-d6) δ 13.23-12.32 (IH),
( ( trifluoromethy 1. ) sulfinyl )phenyl ) -4- 7.67-7.96 (m, 4H); LCMS (M-l): 421.80
(difluoromethyl)- 1 ,2,3-thiadiazole-5
carbothioamide
338 ! N-(2-bromo-4- -NMR (400 MHz, CDC13) δ 9.78 (s, I H), 8.95 (d, J
( ( trifluoromethy 1 ) sulf on y I )ph en yl ) - 4- 5.7 Hz, IH), 8.35 (d, J = 2.0 Hz, IH), 8.07 (dd, J = (difluoromethyl)- 1 ,2,3-thiadiazole-5- ., 1.9 Hz, IH), 7.46 (t, J = 53.5 Hz, IH); LCMS carbothioamide -1): 481.70
N-(2,6-dibromo-4- (400 MHz, CDC13) δ 10.63 (IH), 7.96 (s, ((trifluoromethyl)thio)phenyl)-4- 7.50 (t, J = 53.6 Hz, IH); LCMS (M-l ): 527.60 (difluoromethyl)- 1 ,2,3-thiadiazole-5
carbothioamide
340 ! 4-(difluoromethyl)-N-(4- IH-NMR (400 MHz, DMSO-d6) δ 1 1.55 (s, IH), 8.01
((difluoromethyl)sulfonyl)phenyl)- (t, J = 10.1 Hz, 4H), 7.63 (t, J = 52.7 Hz, I H), 7.27 (t, J 1.2,3-thiadiazole-5-carboxamide = 52.2 Hz, IH); LCMS (M-l): 367.85
4-(difluoromethyl)-N-(4- IH-NMR (400 MHz, DMSO-d6) δ 13.04 (s, IH), 8.28 ((difluoromethyl)sulfonyl)phenyl)- (s, 2H), 8.08 (d, J = 7.9 Hz, 2H), 7.64 (t, J = 52.5 Hz, 1 ,2,3-thiadiazole-5-carbothioamide IH), 7.33 (t, J - 52.1 Hz, IH); LCMS (M-l ): 383.80
342 ! 4-(chloromethyI)-N-(3- ■NMR (400 MHz, CDCI3) δ 8.32 (s, IH), 7.68 (s,
(trifluoromethoxy)phenyl)- 1 ,2,3 - , 7.41-7.48 (m, 2H), 7.10-7.13 (m, IH), 5.29 (s. thiadiazole-5-carbox amide
343 ! N-(2-chloro-4- I H-NMR (400 MHz, DMSO-d6) δ 7.12-7.40 (m, 3H),
((difl.uoromethyl)thio)phenyl)-4- 6.80 (d, J = 8.4 Hz, IH), 5.88 (s, 2H); LCMS (M-2):
(difluoromethyl)- 1 ,2,3-thiadiazoIe-5- 369.75
carboxamide
4-(difluoromethyl)-N-(4- R (400 MHz, DMSO- ) δ 1 1.34 (s, I H), 7.93
((difl uoromethy 1 ) sulf iny 1 ) heny ] (d, J = 8.7 Hz, 2H), 7.80 (d, J = 8.7 Hz, 2H), 7.63 (t, J =
1 ,2.3 - thiadiazole- 5 -c arboxamide 52.8 Hz, I H), 6.95 (t, ./ = 54.0 Hz, IH); LCMS (M-l ):
351.80
345 ! N-(2.6-dichlo3O-4- ¾-NMR (400 MHz, DMSO- ) δ 11.41 (s, IH), 7.85
(trifluoromethoxy)phenyl)-4- (s, 2H), 7.61 (t, J = 52.9 Hz, IH); LCMS (M-l ): 405.7 (difluoromethyl)- 1 ,2,3-thiadiazole-5- carboxamide
N-(2.4-dichloro-6- ¾-NMR (400 MHz, DMSO- ) δ 11.35 (s, IH), 7.95 (trifluoromethoxy)phenyl)-4- (d, ./ = 1.8 Hz, IH), 7.77 (s, IH), 7.61 (t, ./ = 53.1 Hz, (difluoromethyl)- 1 ,2,3 -thiadiazole - 5 - IH); LCMS (M-l): 405.7
carboxamide
4-(difluoromethyl)-N-(4- ¾-NMR (400 MHz, DMSO- ) δ 12.74 (s, IH), ((difluoromethyl)sulfinyl)phenyl)- (d, ./ = 8.4 Hz, 2H), 7.37-7.73 (m, 4H)
l,2,3 hiadiazole-5-carbothioamide 348 N-(2-chloro-4- 1H-NMR (400 MHz, DMSO-d6) δ 1 1.04 (s, I H), 8.03
(trifluoromethyl)phenyl)-4- (d, J = 1.4 Hz, IH), 7.95 (d, J = 8.3 Hz, I H), 7.82 (dd, J (chloromethyl)- 1 ,2,3-thiadiazole-5- = 8.6, 1.5 Hz, IH), 5.33 (s, 2H); LCMS (M-2): 353.75 carboxamide
349 N-(2-chloro-4- 'H-NMR (400 MHz, DMSO-^) δ 12.60 (s, IH),
(difluoromethoxy)phenyl)-4- 7.17-7.74 (m, 5H); LCMS (M-l): 369.85
(difluoromethyl)- 1 ,2,3-thiadiazoIe-5- carbothioamide
350 N-(2,6-dibromo-4- 1 H-NMR (400 MHz, DM S< )-</„) δ 12.91 (s, 2H), 12.53
(trifluoromethyl)phenyl)-4- (t, / = 52.0 Hz, IH ); LCMS (M-l): 495.65
(difluoromethyl)- 1 ,2,3-thiadiazoIe-5- carbothioamide
351 N-(2-bromo-6-chloro-4- Ή-NMR (400 MHz, DMSO- 6) δ 8.09 (s, IH), 8.01
(trifluoromethyl)phenyl)-4- (s, I H), 7.79 (t, J = 53.5 Hz, IH); LCMS (M-l ): 451.70 (difluoromethyl)- 1 ,2,3-thiadiazoIe-5- carbothioamide
352 N-(2-bromo-6-fluoro-4- Ή-NMR (400 MHz, DMSO- ) δ 8.00 (s, IH), 7.894
(trifluoromethyl)phenyl)-4- (s, IH), 7.768 (t, J = 53.2 Hz, I H); LCMS (M-l): (difluoromethyl)- 1 ,2,3-thiadiazoIe-5- 435.80
carbothioamide
353 N-(3,5-dibromopyridin-2-yl)-4- Ή-NMR (400 MHz, DMSO- ) δ 11.69 (s, IH), 8.65 (difluoromethyl)- 1 ,2,3-thiadiazole-5- (d, ,/ = 1.6 Hz, IH), 8.40 (d, J = 2.8 Hz, I H), 7.599 (t, ./ carboxamide = 52.8 Hz, IH); LCMS (M-l): 412.70
354 4-(difluoromethyl)-N-(4-nitro-3- 'H-NMR (400 MHz, DMSO-^) δ 11.70 (s, IH), 8.31
(trifluoromethyl)phenyl)- 1 ,2,3- (d, J = 2.0 Hz, 1 H), 8.28 (d, ,/ = 8.9 Hz, 1 H), 8.12 (dd, J thiadiazole-5-carboxamide = 8.9, 2.2 Hz, IH), 7.64 (t, J = 52.7 Hz, I H); LCMS
(M-l ): 366.85
355 N-(2-cycl.opropyl-4- Ή-NMR (400 MHz, 1 )MS( ) ·· /,, } δ 10.87 (s, IH),
(trifluoromethyl)phenyl)-4- 7.52-7.78 (m, 3H), 7.29 is, IH), 2.07-2.11 (m, I H),
(difkioromethyl)- 1 ,2,3 -ihiadiazole-5- 0.95-0.99 (m, 2H), 0.71-0.75 (m, 2H); LCMS (M-l): carboxamide 361.95
356 4-(difluoromethyl)-N-(2-fluoro-5- ' H-NMR (400 M Hz, OMSO-d6) δ 1 1 .226 (s, I H),
(trifluoromethyl)phenyl)- 1 ,2,3- 8.308 (d, / = 5.2 Hz, I H), 7.49-7.75 (m, 3H); thiadiazole-5-carboxamide LCMS(M-l): 339.80
357 N-(5-chloro-6-(methylthio)pyridin-3- 1 H-NMR (400 MHz, DMSO- ) δ 11.32 (s, IH), 8.65 yl)-4-(difluoromethyl) - 1 ,2,3- (d, J = 2.1 Hz, IH), 8.21 (d, J = 2.1 Hz, IH), 7.62 (t, ./ = thiadiazole-5-carboxamide 52.7 Hz, IH), 2.53 (s, 3H); LCMS (M-l): 334.75
358 N-(2-bromo-4- 1 H-NMR (400 MHz, DMSO-ii6) δ 10.92 (s, IH),
(difluoromethoxy)phenyl)-4- 7.13-7.74 (m, 5H); LCMS (M-l): 399.8
(difluoromethyl)- 1 ,2,3-thiadiazoIe-5- carboxamide
359 N-(2-bromo-4- 1 H-NMR (400 MHz, DMSO-ii6) δ 12.62 (s, IH),
(difluoromethoxy)phenyl)-4- 7.18-7.74 (rn, 5H); LCMS (M-l): 415.7
(difluoromethyl)- 1 ,2,3-thiadiazoIe-5- carbothioamide
360 N-(2,4-dichloro-5- 1 H-NMR (400 MHz, DMSO- ) δ 12.76 (s, IH), 8.00
(difluoromethoxy)phenyl)-4- (s, IH), 7.79 (s, IH), 7.59 (d, J = 53.3 Hz, IH), 7.29 (t,
(difluoromethyl)- 1 ,2,3-thiadiazoIe-5- 7 = 72.7 Hz, IH); LCMS (M-l): 403.75
carbothioamide 361 N-(2,6-dibromo-4- 1H-NMR (400 MHz, DMSO-i¾s) δ 11.65 (s, I H), 8.28
( ( trifluoromethy 1) sulfinyl)phenyl) - 4 - (s, 2H), 7.63 (t, J = 52.9 Hz, IH); LCMS (M-l ): 528.2
(difluoromethyl)- 1 ,2,3-thiadiazoIe-5- carboxamide
362 N-(2,6-dibromo-4- 'H-NMR (400 MHz, DMSO-i¾s) δ 11.89 (s, I H), 8.52 ((trifluoromethyl)sulfonyl)phenyl)-4- (s, 2H), 7.51-7.78 (m, IH); LCMS (M-l): 544, 10 (difluoromethyl)- 1 ,2,3-thiadiazole-5- carboxamide
363 N-(2-bromo-6-chloro-4- 'H-NMR (400 MHz, DMSO-i¾s) δ 11.54 (s, I H), 8.16 ((trifluoromethyl)thio)phenyl)-4- (d, J = 1.7 Hz, IH), 8.09 .\. J = 1.7 Hz, IH), 7.62 (t, ./ = (difluoromethyl)- 1 ,2,3-thiadiazole-5- 52.9 Hz, IH); LCMS (M-l): 467.65
carboxamide
364 N-(2,6-dichloro-4- Ή-NMR (400 MHz, OMSO-d6) δ 11.53 (s, IH), 8.06 ((trifluoromethyl)thio)phenyl)-4- (s, 2H), 7.62 (t, J = 52.9 Hz, IH); LCMS (M-l ): 423.2 (difluoromethyl)- 1 ,2,3-thiadiazole-5- carboxamide
365 N-(2-bromo-6-chloro-4- ¾-NMR (400 MHz, DMSO- ) δ 8.10 (s, IH), 8.02 ((trifluoromethyl)thio)phenyl)-4- (s, 2H), 7.71 (t, J = 52.9 Hz, IH); LCMS (M-l ): 483.70 (difluoromethyl)- 1 ,2,3-thiadiazole-5- carbothioamide
366 N-(2,6-dichloro-4- ¾-NMR (400 MHz, DMSO-i¾) δ 12.04 (s, IH), 7.98 ((trifluoromethyl)thio)phenyl)-4- (s, 2H), 7.71 (t, J = 53.1 Hz, IH); LCMS (M-l ): 437.75 (difluoromethyl)- 1 ,2,3 -thiadiazole - 5 - carbothioamide
367 N-(benzo[d]isothiazol-5-yl)-4- ¾-NMR (400 MHz, DMSO- ) δ 11.30 (s, IH), 9.16 (difluoromethyl)- 1 ,2,3-thiadiazole-5- (d, J = 0.5 Hz, I H), 8.66 (d, J = 1.7 Hz, IH), 8.21 (d, / carboxamide = 8.7 Hz, IH), 7.54-7.80 (m, 2H); LCMS (M-l):
339.85
368 N-(5-chloro-6- Ή-NMR (400 MHz, DMSO- ) δ 11.77 (s, IH), 8.77
(methylsulfonyl)pyridin-3-yl)-4- (d, J = 2.1 Hz, IH), 8.49 (d, J = 2.0 Hz, IH), 7.63 (t, J = (difluoromethyl)- 1 ,2,3-thiadiazole-5- 52.7 Hz, IH), 3.43 (s, 3H); LCMS(M-l): 366.80 carboxamide
369 (4-(difluoromethyl)- 1 ,2,3 -thiadiazol- 1H-NMR (400 MHz, D M SO -Y/,, ) δ 7.26-7.52 (m, 2H), 5-yl)(2,2,4-tri.methylquinolin- 1 (2H)- 7.15 (td, J = 7.5, 1.2 Hz, I H), 6.95 (id, / = 7.7, 1.4 Hz, yl)methanone IH), 6.87 (dd, J = 7.9, 1.1 Hz, IH), 5.79 (d, J = 1.4 Hz,
I H), 2.06 (d, J = 1 .4 Hz, 3H), 1.54 (s, 6H); GCMS(M): 335.1
370 N-(3-chlorophenyl)-4- Ή-NMR-NMR (400 MHz, DMSO-ii6) δ 7.35-7.67 (fluoromethyl)-N -methyl - 1 ,2,3 - (m, 5H), 3.38 (s, 3H); LCMS (M+l ): 304.05 thi adiazo 1 e-5 - carbox amide
371 4-(difluoromethyl)-N-(2-fluoro-3- : ! l-KMRi 4(K) MHz, DMSO- ) 11.22 (s, I H), 8.12 (trifluoromethyl)phenyl)- 1 ,2,3- (t, J = 7.5 Hz, IH), 7.46-7.76 (m, 3H); LCMS (M-l): thiadiazole-5-carboxamide 339.8
372 (4-(di.fluoromethyl)-l,2,3-thiadiazol- 1H-NMR-NMR (400 MHz, OMSO-ek) δ 7.53-7.71( 5-yl)(3 ,4-dihydroquinolin- 1 (2H)- 5H), 3.79 (rn, 2H), 2.76-2.79 (m, 2H), 1.95-1.92 (m, yl)methanone 2H); LCMS (M+l ): 296.3
373 N-(2,4-dichlorophenyl)-4- 1H-NMR (400 MHz, OM$0-d6) δ 7.82 (d, J = 2.3 Hz, (difluoromethyl)-N-methyl- 1 ,2,3- IH), 7.73 i d. J - 8.6 Hz, I H), 7.43-7.70 (m, 2H), 3.32 thi adiazo 1 e-5 -carbox amide (s, 3H); LCMS (M-l): 336.91 N-(4-chloro-3-fluorophenyl)-4- 'H-NMR (400 MHz, OMSO-d6) δ 11.28 (s, IH), 7.79 (difluoromethyl)- l,2,3-thiadiazoIe-5- (dd, J = 11.5, 2.4 Hz, IH), 7.48-7.75 (m, 2H), 7.44 (dd, carbox amide J = 8.9, 1 .4 Hz, I H); LCMS (M-l): 305.75
375 N-(3-chloro-4-fluorophenyl)-4- Ή-NMR (400 MHz, ΌΜΗΟ- , ) δ 11.18 (s, IH), 7.95 (difluoromethyl)- 1 ,2,3-thiadiazole-5- (dd, J = 6.8, 2.5 Hz, IH), 7.43-7.75 (m, 3H); LCMS carboxamide (M-l): 305.80
376 N-(2,4-dibromophenyl)-4- Ή- MR (400 MHz, DMSO- ) δ 8.06 (d, J - 2.1 Hz, (difluoromethyl)-N-methyl- 1 ,2, IH), 7.75 (dd, 7 = 8.4, 2.1 Hz, IH), 7.45-7.71 (m, 2H), thi adiazo 1 e-5 - carbox amide 3.31 (s, 3H); LCMS (M- l ): 425.8
377 5-(3-((difluoromethyl)thio)phenyl)- R (400 MHz, DMSO-ii6) δ 8.17 (s, I H), 7.92 4,5 -di ydro-6H-pyrrolo [ 3,4- (d, IH), 7.69-7.41 (m, 3H), 5.50 (s, 2H); GCMS: d] [l jihiadiazol-6-one
378 4-(difluoromethyl)-N-methyl-N- Ή-NMR (400 MHz, PMSO-.vV, } δ 7 '.95-7 '.96 (m, 2H), (2,4,6-trichlorophenyl)- 1 ,2,3- 7.46-7.73 (m, I H), 3.31 (s, 3H); LCMS (M-l): 370.22 thiadiazole-5-carboxamide
379 N-(4-chloro-3-fluorophenyl)-4- 1H-NMR (400 MHz, DMSO-i¾) δ 12.81 (s, I H)
(difkioromethyl)- 1 ,2,3-thiadiazole-5- (dd, J = 11.1, 2.1 Hz, IH), 7.47-7.73 (m, 3H);
carbothioamide (M-l): 321.75
38( N-(3-chloro-4-fluorophenyl)-4- !R (400 MHz, DMSO- ) '> 12.72 (s, I H), 8.19
(difluoromethyl)- l,2,3-thiadiazole-5- (dd, ./ - 6.8, 2.5 Hz, IH), 7.47-7.75 (m, 3H); LCMS carbothioamide (M-l): 321.75
m N-(4-chloro-2-cyclopropylphenyl)-4- {H-NMR (400 MHz, DMSO-ii6) δ 10.72 (s, IH), (difluoromethyl)- l,2,3-thiadiazoIe-5- 7.47-7.76 (m, 2H), 7.28 (dd, J = 8.5, 2.4 Hz, IH), 7.02 carboxamide (d, ./ = 2.3 Hz, I H), 1 .97-2.03 (m, I H), 0.90-0.95 (m,
2H), 0.67-0.71 (m, 2H); LCMS (M-l): 327.90
382 N-(2-bromo-4- Ή-NMR (400 MHz, OMSQ~d6) δ 12.78 (s, IH), 8.14
((trif luoromethyl) su If in yl )phenyl ) -4- (s, IH), 7.55-7.86 (m, 3H); LCMS (M-l): 466.25 (difluoromethyl)- l,2,3-thiadiazole-5- carbothioamide
383 N-(2,6-dichloro-4-(pentafluoro-16- Ή-NMR (400 MHz, OMSQ~d6) δ 12.16 (s, IH), 8.1 1 sulfaneyl)phenyl)-4- (s, 2H), 7.85 (t, J = 53.3 Hz, IH); LCMS (M-l): 463.75 (difluoromethyl)- l,2,3-thiadiazole-5- carbothioamide
384 N-(2-bromo-6-chloro-4-(pentafluoro- Ή-NMR (400 MHz, DMSO-ii6) .) 1 i .67 (s, I H), 8.37 16-sulfaneyl)phenyl)-4- (d, ./ = 16.5 Hz, 2H), 7.64 (t, J = 53.0 Hz, I H); LCMS (difluoromethyl)- 1 ,2,3-thiadiazole-5- (M-l): 493.7
carboxamide
385 N-(2,6-dichloro-4-(pentafluoro-16- Ή-NMR (400 MHz, DMSO-^) δ 8.42 (d, ./ = 0.9 Hz, sulfaneyl)phenyl)-4- 2H), 7.59 (t, ./ = 52.4 Hz, IH), 3.31 (s, 3H);
(difl uorometh y 1 )-N-methy 1 -1 ,2,3- thiadiazole-5-carboxamide
386 N-(2-cyclopropyl-4-(pentafluoro-16- Ή-NMR (400 MHz, DMSO-ii6) .) 10.89 (s, I H), 7.80 sulfaneyl)phenyl)-4- (s, 2H), 7.65 (t, J = 52.9 Hz, IH), 7.41 (s, I H), (difluoromethyl)- 1 ,2,3-thiadiazole-5- 2.08-2.12 (m, IH), 0.96-1.01 (m, 2H), 0.69-0.73 (m, carboxamide 21 I S: LCMS (M-l): 419.9
387 N-(2-bromo-6-chloro-4- 'H-NMR (400 MHz, OMSO-de) δ 11.64 (s, IH), 8.24 ((trifluoromethyl)sulfinyl)phenyl)-4- (s, IH), 8.17 (s, IH), 7.63 (t, ./ = 52.9 Hz, IH); LCMS (difluoromethyl)- l,2,3-thiadiazole-5- (M-l): 483.70
carboxamide 388 N~(2,6-dichloro-4~ 1H-NMR (400 MHz, OMSO-d6) δ 11.63 (s, I H), 8.15
( ( trifiuoromethy 1) sulfinyl)phenyl) - 4 - (s, 2H), 7.64 (t, J = 52.9 Hz, IH); LCMS (M-1 ): 439.2
(difluoromethyl)- 1 ,2,3-thiadiazole-5- carboxamide
389 N-(2,6-dibromo-4- XH-NMR (400 MHz, CDC13) δ 9.17 (s, IH), 7.97 (s,
( ( trifluoromethy 1) sulfinyl)phenyl) - 4 - 2H), 7.49 (t, J = 53.5 Hz, IH); LCMS (M-1): 545.15
(difluoromethyl)- 1 ,2,3-thiadiazoIe-5- carbothioamide
390 N-(2-bromo-6-chloro-4- XH-NMR (400 MHz, CDCI3) δ 9.16 (s, IH), 7.92 (s, ((trifluoromethyl)sulfinyl)phenyl)-4- IH), 7.80 (s, IH), 7.48 (t, ./ = 53.6 Hz, IH); LCMS (difluoromethyl)- 1 ,2,3-thiadiazoIe-5- (M-1): 499.6
carbothioamide
391 N-(2,6-dichloro-4- Ή-NMR (400 MHz, CDC13) δ 9.15 (s, IH), 7.76 (s, ((trifluoromethyl)sulfinyl)phenyl)-4- 2H), 7.48 (t, J = 53.6 Hz, IH); LCMS (M-1): 456.01 (difluoromethyl)- 1 ,2,3-thiadiazole-5- carbothioamide
392 N-cyclopropyl-N-(3,5- Ή-NMR (400 MHz, OMSO-d6) S 7.53-7.76 (ni, 4H), dichlorophenyl)-4-(difluoromethyl)- 3.19 (m, IH), 0.52-0.70 (m, 4H); LCMS (M-1 ): 363.19 l,2,3-thiadiazole-5-carboxaniide
393 N-(2-bromo-4- 1H-NMR (400 MHz, DMSO-d6) δ 10,99 (s, IH), 7.94
((difluoromethyl)thio)phenyl)-4- (d, J = 1.8 Hz, IH), 7.43-7.77 (m, 4H); LCMS(M+0): (difluoromethyl)- 1 ,2,3-thiadiazole-5- 415.75
carboxamide
394 4-(difluoromethyl)-N-(2- 1 H-NMR (400 MHz, DMSO-d6) δ 11.05 (s, IH), ((difl.uoromethyl)thio)phenyl)- 1 ,2,3- 7.25-7.74 (m, 6H); LCMS (M-1): 335.75
thiadiazole-5-carboxamide
395 4-(difluoromethyl)-N-(2- 1H-NMR (400 MHz, DMSO-d6) δ 12.81 (s, IH), ((difluoromethyl)tliio)phenyl)- 1 ,2,3- 7.28-7.78 (m, 6H); LCMS (M-1): 351.80
thiadiazole-5-carbothioamide
396 N-(2-chloro-4- 1H-NMR (400 MHz, DMSO-d6) δ 12.71 (s, IH),
((difluoromethyl)thio)phenyl)-4- 7.38-7.81 (m, 5H); LCMS (M-2): 385.85
(difluoromethyl)-- 1 ,2,3 -ihiadiazok 5- carbothioamide
397 N-(4-chloro-2- 1H-NMR (400 MHz, DMSO-d6) δ 1 1.10 (s, I H),
((difluoromethyl)thio)phenyl)-4- 7.35-7.75 (m, 6H); LCMS (M- 1): 369.85
(difkioromethyl)- 1 ,2,3 -ihiadiazok 5- carboxamide
398 N-(4-bromo-2- 1H-NMR (400 MHz, DMSO-d6) δ 1 1.08 (s, I H), 7.88
((difluoromethyl)thio)phenyl)-4- (d, J = 2.3 Hz, IH), 7.79 (dd, J = 8.6, 2.3 Hz, IH),
(difkioromethyl)- 1 ,2,3 -ihiadiazok 5- 7.34-7.73 (m, 3H); LCMS (M+0): 415.80
carboxamide
399 N-(2-chloro-4- 1H-NMR (400 MHz, DMSO-d6) δ 1 1.10 (s, I H), 8.07
((difluoromethyl)sulfinyl)phenyl)-4- (d, J = 8.4 Hz, IH), 7.96 (d, J = 1.8 Hz, IH), 7.82 (dd, J
(difkioromethyl)- 1 ,2,3 -ihiadiazole-5- = 8.5, 1.8 Hz, IH), 7.63 (t, J = 52.9 Hz, I H), 7.05 (t, J = carboxamide 53.7 Hz, IH); LCMS (M-2): 385.80
400 N-(4-chloro-2- 1H-NMR (400 MHz, DMSO-d6) δ 12.85 (s, IH),
((difluoromethyl)tliio)phenyl)-4- 7.38-7.80 (111, 5H); LCMS (M-2): 385.85
(dif uoromethyl)- l,2,3-thiadiazole-5- carbothioamide 401 N-(2-chloro-4- 1H-NMR (400 MHz, DMSO-d6) δ 1 1.20 (s, I H), 8.29
((difluoromethyl)sulfonyl)phenyl)-4- (d, J = 8.6 Hz, IH), 8.1 1 (d, J = 2.1 Hz, I H), 8.05 (dd, J (difluoromethyl)- 1 ,2,3-thiadiazole-5- = 8.6, 2.1 Hz, I H), 7.64 (t, J = 52.9 Hz, IH), 7.38 (t, J = carboxamide 52.1 Hz, IH); LCMS (M-2): 401 .80
402 4-(difluoromethyl)-N-(2- 1H-NMR (400 MHz, DMSO-d6) δ 1 1.39 (s, I H), 7.91 ((difluoromethyl)sulfinyl)phenyl)- (d, J = 7.9 Hz, I H), 7.48-7.77 (m, 4H), 7.02 (dd, .1 = 1 ,2, 3 -thiadiazole-5 -carboxamide 54.7, 53.5 Hz, IH); LCMS (M-1): 351.82
403 (4-(difluoromethyl)-l,2,3-thiadiazol- Ή-NMR-NMR (400 MHz, DMSO-ii6) δ 7.26-7.52 5-yl)(2,2,4-trimethyl-3,4- (m, 2H), 7.14-7.18 (m, IH), 6.87-6.94 (m, 2H), 2.93 dihydroquinolin- l(2H)-yl)methanone (dd, J = 9.9, 6.5 Hz, IH), 2.00 (dd, J = 13.0, 2.6 Hz,
IH), 1 .73 is, 3H), 1 .51 (s, 3H), 1.32 (d, J = 6.9 Hz, 3H), 1.19 (t, J = 12.5 Hz, I H); GCMS ( M S: 337.1
404 4-(fluoromethyl)-N-(3- Ή-NMR (400 MHz, DMSO- ) <5 11.16 (s, IH), 8.11 (trifluoromethyl)phenyl)- 1 ,2,3- (s, IH), 7.86 i d. ./ = 7.9 Hz, IH), 7.58-7.63 (m, IH), thiadiazole-5-carboxamide 7.50 (t, J = 7.7 Hz, IH), 5.94 (d, J = 47.2 Hz
LCMS(M-i): 303.85
405 N-cyclopropyl-4-(difluoromethyl.)- :, OMSO-de) δ 7.29-7.73 (m, 5H), N-(3-((rifluoromethoxy)phenyl)- 3.23 (d, J = 20.6 Hz, IH), 0.51 -0.82 (m, 4H); LCMS 1.2,3-thiadiazole-5 -carboxamide (M-1): 379.3
406 N-cyclopropyl-4-(difluoromethyl)- R (400 M Hz, DMSC s) δ 7.30-7.78 (m, 5H), N - ( 4-(tri fluoromethox y )pheny 1 ) - 3.22-3.19 (m, IH), 0.53-0.84 (m, 4H); LCMS (M-1): 1 ,2,3-thiadiazole-5-carboxamide 379.3
407 N-cyclopropyl-4-(difluoromethyl)- 1 H-NMR (400 MHz, DMSO-d6) δ 7.30-7.75 (m, 5H), N - ( 3 - (tri fluoromethox y )pheny 1 ) - 3.73 (t, J = 3.4 Hz, I H), 1.01 (d, J = 6.4 Hz, IH), 0.65 l,2.3-thiadiazole-5-carbothioamide (d, J = 28.1 Hz, 3H); LCM S (M- 1 ): 395.3
408 N-cyclopropyl-4-(difluoromethyl)- IR (400 MHz, DMSO-<¾$) δ 7.83-7.22 (5H)
N-(4-(trifluoromethoxy)phenyl)- 3.82-3.68 (IH), 1.06-0.91 (I H), 0.75-0.56 (3H) l,2.3-thiadiazole-5-carbothioarnide LCMS (M-1): 395.37
409 N-cyclopropyl-4-(difluoromethyl)- {H-NMR (400 MHz, DM SO-,/,, ) δ 7.44-8.02 (m, 5H), N-(3 -(pentafluoro -16- 3.24 (s, IH), 0.49-0.85 (m, 4H); GCMS(M) 421 sulf aneyl)phenyl)- 1 ,2,3-thiadiazole- 5 -carboxamide
410 4-(fluoromei.hyl)-N-(4- Ή-NMR (400 MHz, DMSO- ) δ 11.22 (s, IH), 7.89 (trifluoromethyl)phenyl)- 1 ,2,3- (d, j = 8.6 Hz, 2H), 7.76 (d, J = 8.7 Hz, 2H), 5.96 (d, / thiadiazole-5-carboxamide = 47.4 Hz, 2H); LCMS(M-l): 303.85
411 (4-(diiluoromethyl)- 1 ,2,3 -thiadiazol- XH-NMR-NMR (400 MHz, DMSO-ii6) δ 7.53 (t, ./
5-yl)(8,8-dimethylditliieno[3,2- 53.0 Hz, I H), 7.38 (d, J = 5.3 Hz, 2H), 6.91 (s, 2H b :2',3 '-e]pyridin-4( 8 H)- yl)methanone 1.69 (s, 6H); GCMS (M): 382.9
412 N-(4'-chloro- [ 1 , 1 '-biphenyl] -4-yl)-4- 'H-NMR (400 MHz, DMSO-^) δ 11.11 (s, IH), (difluoromethyl)- l,2,3-tliiadiazole-5- 7.64-7.77 (m, 7! 15. 7.48-7.52 (m, 2H); LCMS (M-1): carbox amide 363.8
413 N-(2,6-dichloro-4- 'H-NMR (400 MHz, DMSO-i¾) δ 11.88 (s, I H), 8.43
((trifluoromethyl)sulfonyl)phenyl)-4- (s, 2H), 7.65 (t, j = 52.9 Hz, IH); LCMS (M-1): 453.80 (difluoromethyl)- 1 ,2,3-thiadiazole-5- carboxamide
414 N-(2-bromo-6-chloro-4- 'H-NMR (400 MHz, DMSO-i¾) δ 11.88 (s, I H), 8.50 ((trifluoromethyl)sulfonyl)phenyl)-4- (s, IH), 8.47 (s, IH), 7.64 (t, ./ = 52.9 Hz, IH); I . CI (difluoromethyl)- 1 ,2,3-thiadiazole-5- (M-1): 499.6
carboxamide 415 N-(2-cyclopropyl-4- 1H-NMR (400 MHz, DMSO-rfi) δ 10.81 (s, IH), ((trifluoromethyl)thio)phenyl)-4- 7.51 -7.78 (m, 3H), 7.30 (d, / = 1.2 Hz, IH), 2.02-2.09 (difluoromethyl)- 1 ,2,3-thiadiazole-5- (m, I H), 0.94-0.99 (m, 2H), 0.66-0.70 (m, 2H); LCMS carboxamide (M-l): 394.10
416 4-(chloromethyl)-N-(4- 1 H-NMR (400 MHz, CDCi3) δ 8.33 (s, IH), 7.71 (s, ((trifluoromethyl)thio)phenyl)- 1,2,3- 4H), 5.30 (s, 2H)
thiadiazole-5-carboxamide
417 4-(chloromethyl)-N-(4-fluoro-3- 1 H-NMR (400 MHz, CDC13) «5 8.30 (s, IH), 7.91 (dd, J (trifluoromethyl)phenyl)- 1 ,2,3- = 5.8, 2.6 Hz, I H), 7.80-7.84 (m, IH), 7.28 id, J = 9.2 thiadiazole-5-carboxamide Hz, IH), 5.30 (s, 2H)
418 4-(chloromethyl)-N-(4- 1 H-NMR (400 MHz, CDC13) δ 8.28 (s, IH), 7.67 (d, J (trifluoromethoxy)phenyl)- 1,2,3- = 9.0 Hz, 2H), 7.29 (s, 2H), 5.29 (s, 2H)
thi adiazo 1 e-5 - carbox amide
419 4-(difluoromethyl)-N-(2- 1 H-NMR (400 MHz, DMSC)-.-/,, ) δ 12.80 (s, IH), ((difluoromethyl)sulfinyl)phenyl)- 7.28-7.77 (m, 6H)
1 ,2, 3 -thiadiazole-5 -carbothioamide
420 N-(2-chloio-4- 1 H-NMR (400 MHz, DMSO-d6) δ 7.86-8.04 (m,
((difluoromethyl)sulfonyl)phenyl)-4- 4H), 7.36 (i, J = 52.1 Hz, IH); LCMS (M-2): 417.80 (difluoromethyl)- 1 ,2,3-thiadiazole-5- carbothioamide
421 N-(3-(4-chlorophenoxy)phenyl)-4- 1 H-NMR (400 MHz, DMSO-d6) δ 1 1 .05 (s, I H), (difluoromethyl)- 1 ,2,3 -thiadiazole - 5 - 7.35-7.73 (m, 6H), 7.07 (d, J = 8.9 Hz, 2H), 6.86-6.88 carbox amide (m, I H); LCMS! M -2 ); 379.85
422 4-(difluoromethyl)-N-(3- 1 H-NMR (400 MHz, DMSO-d6) δ 1 1 .03 (s, I H), phenoxyphenyl)- 1 ,2,3 -thiadiazole-5- 7.59 (t, J = 52.8 Hz, I H), 7.30-7.43 (m, 5Ή), 7.15-7.18 carboxamide (m, I H), 7.05 (d, .1 = 7.8 Hz, 2H), 6.84 (dd, J = 7.7, 0.8
Hz, IH); LCMS (M-l): 345.85
423 N-(3-(3,4-dichlorophenoxy)phenyl)- l H-NMR (400 MHz, DMSO-d6) δ 1 1.08 (s, IH),
4- (difluoromethyl)- 1 ,2,3-thiadiazole- 7.40-7.73 (m, 5H), 7.35 (d, J = 2.8 Hz, IH), 7.05 (dd, J
5- carboxamide = 8.9, 2.9 Hz, I H), 6.91-6.93 (m, IH); LCMS (M-2):
413.80
424 4-(difluoromethyl)-N'-phenyl- 1 ,2,3- 1 H-NMR (400 MHz, DMSO-d6) δ 7.84 (t, J - 53 ,6 thiadiazole- 5 - carbohydrazide Hz, IH), 7.63-7.66 (m, 2H), 7.44-7.48 (m, 2H), 7.30 (t,
J = 7.3 Hz, IH), 6.48 (s, 2H); LCM S (M- l ): 268.80
425 N'-(4-chlorophenyl)-4- 1 H-NMR (400 MHz, DMSO-d6) 6 7.68-7.95 (m, (difluoromethyl)- 1 ,2,3-thiadiazole-5- 3H), 7.52-7.55 (m, 2H), 6.48 (s, 2H); LCMS (M-2): carbohydrazide 302.85
426 4-(chloromethyl)-N-(3- 1 H-NMR (400 MHz, CDC13) δ 8.27 (s, IH), 7.96 (s, ((trifluoromethyl)thio)phenyl)- 1 ,2,3- IH), 7.77 i d. ./ = 7.9 Hz, IH), 7.54 (d, ./ = 7.8 Hz, I H), thiadiazole-5-carboxamide 7.48 (t, J = 7.9 Hz, IH), 5.31 is, 2H)
427 4-(thiocyanatomethyl)-N-(4- 1 H-NMR (400 MHz, DM SO ·· /,, } δ 11.09 (s, IH), (trifluoromethoxy)phenyl)- 1,2,3- 7.76-7.80 (m, 2H), 7.39-7.42 (m, 2H), 4.97 (s, 2H) thiadiazole-5-carboxamide
428 N-(4-fluoro-3- 1 H-NMR (400 MHz, CDC13) <5 8.10 (s, I H), 7.89 (dd, J
( trifluoromethy 1 )p heny 1 )-4- = 5.9, 2.5 Hz, IH), 7.76 (dt, J = 8.8, 3.5 Hz, IH), 7.23
(thiocyanatomethyl)- 1,2,3- (d, J - 9.3 Hz, IH), 4.90 (d, J = 15.0 Hz, 2H) thiadiazole-5-carboxamide
429 4-(thiocyanatomethyl)-N-(3- 1 H-NMR (400 MHz, CDCi3) δ 8.1 1 (s, IH), 7.92 (s, ((trifluoromethyl.)thio)phenyl)- 1 ,2,3- IH), 7.72 (d, 7 = 8.1 Hz, IH), 7.49-7.53 (m, IH), 7.45 thiadiazole-5-carboxamide (t, ,/ = 7.9 Hz, IH), 4.88 (t, J = 15.1 Hz, 2H) 430 4-(thiocyanatomethyl)-N-(4- H-NMR (400 MHz, CDC13) δ S.01 (
((trifluoromethyl)thio)phenyl)- 9.2, 2.5 Hz, 4H), 4.87 (s, 2H)
thiadiazole-5-carboxamide
431 (4-(difluoromethy 1.)- 1 ,2,3 -thiadiazol- Ή-NMR-NMR (400 MHz, DMSQ-i/6) δ 7.04-7.74 ( 5-yl)(3 ,4-dihydroisoquinolin-2( 1 H)- 5H), 4.79 (s, 2H), 3.40-3.43 (m, 2H), 2.77-2.80 (m, yl)methanone 2H); LCMS (M-+1): 296.3
4-(difluoromethyl)-N-methyl-N-(4- 'H-NMR (400 MHz, DMSQ- ) δ 7.71 (d, 7 = 8.4
( ( trifiuoromethyl)thio)phenyl)- 1 ,2,3 - Hz, 2H), 7.37-7.64 (m, 3H), 3.40 (s, 3H); LCMS thiadiazole-5-carboxamide (M-l ): 368.3
433 4-(difluoromethyl)-N-methyl-N-(4- NMR (400 MHz, DMSO- δ 7.89 (d, 7 = ((t"rifluoromethyl)suliinyl)phenyl)- 2H), 7.71 (d, 7 = 8.4 Hz, 2H), 7.51 (t, 7 = 53.0 1 ,2, 3 -thiadiazole-5 -carboxamide , 3.42 (s, 3H); LCMS (M-l): 384.3
434 N'-(3,4-dichlorophenyl)-4- 1H-NMR (400 MHz, DMSO-d6) δ 8.02 (d, J = 2.3 (difluoromethyl)- 1 ,2,3-thiadiazole-5~ Hz, I H), 7.68-7.95 (m, 3H), 6.49 (s, 2H); LCMS carbohydrazide (M-2): 336.80
435 4-(difluoromethyl)-N-(3- 1H-NMR (400 MHz, DMSO-d6) δ 1 1.17 (s, IH), ((difluoromethyl)tliio)phenyl) 7.96 (t, J = 1.8 Hz, IH), 7.36-7.76 (m, 5H); LCMS thiadiazole-5 -carboxamide (M-l): 335.80
436 4-(difluoromethyl)-N-(3- Ή-NMR (400 MHz, DMSO-,-/,,, } δ 7.57-7.86 (m, I H), ((trifluoromethyl)thio)phenyl)-l 7.50 (t, 7 = 7.8 Hz, IH), 7.38 (d, 7 = 7.6 Hz, IH), 7.30 thiadiazole-5 -carboximidamide (s, I H), 7.13-7.26 (m, 3H); LCMS (M-l): 352.80
437 4-(difluoromethyl)-N-(3- Ή-NMR (400 MHz, DMSO-tfc) δ 7.74 (t, 7 = 52.7 Hz (trifluoromethyl)phenyl)- 1 ,2,3- IH), 7.55 (t, ,/ = 7.9 Hz, I H), 7.38 (d, ./ = 7.6 Hz, IH) thiadiazole-5 -carboximidamide 7.29 (s, IH), 7.13-7.23 (m, 3H); LCMS (M-l): 320.90
438 4-(difluoromethyl)-N-(3- ¾-NMR (400 MHz, OM$0-d6) δ 7.75 (t, J = 52.7 H
(pentafluoro-16-sulfaneyl)phenyl)- IH). 7.49-7.58 (m, 2H), 7.45 (s, I H), 7.21 -7.36 (r l,2,3-thiadiazole-5-carboxiniidamide 3H); LCMS (M- l): 378.90
439 4-(difluoromethyl)-N-(3- Ή-NMR (400 MHz, DMSO-i¾) δ 7.70 (t, 7 = 52.8 Hz fluorophenyl.)- 1 ,2,3-thiadiazole-5- IH), 7.33-7.38 (m, I H), 7.14 (s, 2H), 6.83-6.88 (m carboximidamide ), 6.76-6.81 (m, 2H); LCMS (M-l): 270.85
440 N-(3 -bromo phenyl )-4- Ή-NMR (400 MHz, DMSO-£¼) δ 7.70 (t, J = 52.8 Hz, (difluoromethyl)- 1 ,2,3-thiadiazole-5- IH), 7.29 (t, 7 = 7.9 Hz, IH), 7.21-7.23 (m, I H), 7.17 carboximidamide (t, ,/ = 1.8 Hz, 3H), 6.92-6.94 (m, I H); LCMS (M-l ):
332.75
441 N-([ l ,r-biphenyl]-4-yl.)-4- 1R (400 MHz, DMSO-,/,, ) δ 1 1 .10 (s, I H)
(difluoromethyl)- l,2,3-thiadiazole-5- 7.51 -7.78 (m, 7H), 7.44-7.49 (m, 2H), 7.33-7.37 (m carboxamide IH); LCMS (M-l): 329.8
N-(4-cyanophenyl)-4- XH-NMR (400 MHz, DMSO- ) δ 11.37 (s, IH),
( difluoromethyi)- 1 ,2,3 -thiadiazole- 5 - 7.86-7.90 (m, 2H), 7.83 (dd, 7 - 6.8, 2.4 Hz, 2H), 7.62 carboxamide (t, 7 = 52.8 Hz, I H); LCMS (M-l): 278.8
443 N-(4-bromo-2- Ή-NMR (400 MHz, DMSO -//,,) δ 12.58 (s, IH) (trifluoromethyl)phenyl)-4- 8.01-8.03 (m, 2H), 7.64 (d, J = 9.3 Hz, I H), 4.33 (s (morpholinomethyl)- 1 ,2,3- 2H), 3.46 (s, 4H). 2.52 (t, J = 4.5 Hz, thi adiazo 1 e-5 - carbox amide LCMS(M- l): 450.90
444 4-(morpholinomethyl)-N-(3- R (400 MHz, DMSO- ) δ 12.36 (s, I H), 8.25 (penta.il uoro - 16 - sulf aney 1 )p heny 1 (t, J = 2.0 Hz, IH), 7.84 (d, J = 7.9 Hz, IH), 7.74 (dq, J 1 ,2.3 - thiadiazole- 5 -c arboxamide = 8.4, 1.1 Hz, IH), 7.69 (t, J = 8.1 Hz, IH), 4.32 (s,
2H), 3.57 (t, J = 4.5 Hz, 4H), 2.52-2.56 (m, LCMS(M+1): 430.95
Figure imgf000120_0001
460 4- ((4-methylpiperazin- 1 -yl)methyl)- 1H-NMR (400 MHz, DMSO-^) δ 12.65 (s, IH), N-(3 -(pentafluoro -16- 8.16-8.17 (m, IH), 7.89-7.91 (rn, IH), 7.69-7.75 (m, sulf aneyl)phenyl)- 1 ,2,3-thiadiazole- 2H), 4.37 (s, 2H), 2.56 (s, 4H), 2.32 (s, 4H), 2.12 (s,
5- carboxamide 3H)
461 N-(3',4'-difluoro - [ 1 , 1 '-biphenyl] -2- 1 H-NMR (400 MHz, DMSO-i ) δ 10.65 (s, IH), 7.63 yl)-4-(dffluoromettiyl) - 1 ,2,3- (d, J = 7.9 Hz, IH), 7.30-7.56 (m, 6H), 7.25 (d, ,/ = thiadiazole-5-carboxamide 3.8 Hz, IH); LCMS (M- l): 365.9
462 4-(difluoromethyl)-N-(thiazol-2-yl)- 1 H-NMR (400 MHz, DMSO-d6) δ 13.75 (s, IH), 1,2, 3 -thiadiazole- 5 - c ar boxamide 7.87 (t, J = 53.3 Hz, I H), 7.59 (d, J = 4.4 Hz, IH), 7.24
(d, J = 4.3 Hz, IH); LCMS (M-l): 260.80
463 4-(difluoromethyl)-N-(lH-pyrazol-3- 1 H-NMR (400 MHz, DMSO-d6) δ 12.60 (s, IH), yl)-l ,2,3-thiadiazole-5-carboxamide 11.72 (s, IH), 7.47-7.74 (m, 2H), 6.61 (s, IH); LCMS
(M- l): 243.90
464 N-(benzo[d]thiazol-2-yl)-4- 1 H-NMR (400 MHz, DMSO-d6) δ 14.14 (s, IH),
(dif uoromethyl)- l,2,3-thiadiazole-5- 8.00 id, I H), 7.98-7.77(t, I H), 7.60 (d, IH), 7.52 (t, carboxamide IH), 7.39(t, IH); LCMS (M-l): 310.85
465 4-(difluoromethyl)-N-(pyridazin-4- 1 H-NMR (400 MHz, DMSO-d6) δ 1 1 .73 (d, J=12.1 yl)-l,2,3-thiadiazole-5-carboxamide Hz, IH), 9.33 (d, J=2.0 Hz, I H), 9.13 (d, 1=5.5 Hz, IH),
7.98 (q, J=2.9 Hz, IH), 7.64 (t, J=52.7 Ηζ, ΙΗ); LCMS (M-l): 243.90
466 N-(3-(trifl.uoromethoxy)phenyl)-4- !l-NMR (400 MHz, DMSO- ) δ 12.95 (s, I H), 8.11 (trifluoromethyl)- 1 ,2,3-thiadiazole-5- (s, IH), 7.78 (dd, J = 8.1, 1.1 Hz, IH), 7.63 (t, / = 8.2 carbothioamide Hz, IH), 7.37 (dt, J = 8.3, 1.1 Hz, IH); LCMS (M-l):
371.9
467 N-(2-chloro-4- 'H-NMR (400 MHz, DMSO-i¾) δ 12.88 (d, / = 1.7
((trifluoromethyl)thio)phenyl)-4- Hz, IH), 8.04 (d, ./ := 1 .5 Hz, IH), 7.88 id, J = 8.4 Hz, (trifluoromethyl)- 1 ,2,3-thiadiazole-5- IH), 7.84 (dd, J = 8.3, 1.5 Hz, IH); LCMS (M-l ): carbothioamide 421.8
468 N-(2-chloro-4- Ή-NMR (400 MHz, DMSO-i/6) δ 12.79 (s, IH), 7.83 (trifluoromethoxy)phenyl)-4- (d, ,/ = 8.9 Hz, I H), 7.80 (d, J = 2.3 Hz, I H), 7.55 (dd, / (trifluoromethyl)- 1 ,2,3-thiadiazole-5- = 8.9, 1.4 Hz, IH); LCMS (M-l): 405.8
carbothioamide
469 N-(4-(trifluoromethoxy)phenyl)-4- Ή-NMR (400 MHz, DMSO- ) ' 12.88 (s, I H), (trifluoromethyl)- 1 ,2,3-thiadiazole-5- 7.96-8.00 (m, 2H ), 7.50 (d, J = 8.4 Hz, 2H); LCMS carbothioamide (M-l): 371.80
470 4-(trifluoromethyl)-N-(3- 'H-NMR (400 MHz, DMSO-i¾s) δ 12.94 (s, I H), 8.34 ((trifluoromethyl)thio)phenyl)- 1 ,2,3 - (s, IH), 8.00 (dd, J = 7.6, 1.8 Hz, IH), 7.64-7.71 (m, thiadiazole-5-carbothioaniide 2H); LCMS (M- l): 388.01
471 N-(2-cyclopropyl-4- Ή-NMR (400 MHz, DMSi >-- /„) δ 12.63 (s, I H), 7.56 (trifluoromethoxy)phenyl)-4- (d, J = 8.7 Hz, IH), 7.29 (dd, J - 8.7, 1.4 Hz, IH), 7.00 (trifluoromethyl)- 1 ,2,3-thiadiazole-5- (d, J = 2.3 Hz, IH), 1.93-2.00 (m, I H), 0.95-1.00 (m, carbothioamide 2H), 0.72-0.76 (m, 2H); LCMS (M-l): 412.01
472 N-(4-chlorophenyl)-4- ' H-NMR (400 MHz, DM SO- δ 12.83 (s, I H), (trifluoromethyl)- 1 ,2,3-thiadiazole-5- 7.88-7.92 (m, 2H), 7.54-7.58 (m, 2H); LCMS (M-l): carbothioamide 321.85
473 4-(trifluoromethyl)-N-(3- Ή-NMR (400 MHz, ΌΜ Ο- , ) δ 13.00 (s, IH), 8.36 (trifluoromethyl)phenyl)- 1 ,2,3- (s, IH), 8.04-8.07 (m, IH), 7.71-7.77 (m, 2H); LCMS thiadiazole-5-carbothioamide (M-l): 356.00
474 N-(3-chlorophenyl)-4- 1 H-NMR (400 MHz, DMSO-i¾s) δ 12.86 (s, I H), 8.09 (trifluoromethyl)- 1 ,2,3 - thiadiazole-5- (t, J = 1.9 Hz, IH), 7.70-7.72 (rn, I H), 7.53 (t, J = 8.1
Figure imgf000122_0001
4-(fluoromethyl)-N-(3-(pentafluoro- 'H-NMR (400 MHz, DMSO-di) δ 11.25 (s, IH), 8.31 16-sulfaneyl)phenyl)- 1 ,2,3- (d, J = 2 Hz, IH), 7. 90 (d, 7 = 8 Hz, IH), 7.72-7.70 thiadiazole-5-carboxamide (m, 2H), 5.96 (d, 7 = 47.2 Hz, 2H); LCMS (M-l):
361.9
N-(3-chlorophenyl)-4- Ή-NMR (400 MHz, DMSQ-i¾) δ 11.05 (s, IH), 7.86 (((trifluoromethyl)thio)methyl)- 0, 7 = 2.0 Hz, IH), 7.58-7.60 (m, IH), 7.44 (t, 7 = 8.2 1 ,2,3-thiadiazole-5-carboxamide Hz, IH), 7.26 (dq, 7 = 8.0, 1.0 Hz, IH), 4.91 (s, 2H);
LCMS (M-l): 351.85
N - ( 3 - (tri fluoromethyl)phen yl) -4- R (400 MHz, DMSO-<¾$) δ 11.16 (s, I H), 8.1 1 (((ixifl u orometh yl) thio)methy 1 ) - , 7.92 (d, 7 = 8.4 Hz, IH), 7.65 (t, 7 = 7.9 Hz, 1,2.3 - thiadiazole - 5 -c arboxamide .54 (d, 7 = 7.8 Hz, IH), 4.91 (s, 2H); LCMS
385.80
N-(4-chlorophenyl)-4- 'H-NMR (400 MHz, OMSO-d6) δ 11.02 (s, IH), 7.72
( ( (trifluoromethy 1) thi o)methyl) - (dd, 7 = 6.7, 2.1 Hz, 2H), 7.47 (dd, 7 = 6.8, 2.2 Hz, 2H),
1 ,2, 3 -thiadiazole- 5 -carboxamide 4.91 (s, 2H); LCMS (M- l): 351.80
4-(((trifluoromethyl)thio)methyl)-N- Ή-NMR (400 MHz, DMSO- ) δ 11.18 (s, IH), 7.86 (4-((trifluoromethyl)thio)phenyl)- (d, 7 = 8.8 Hz, 2H), 7.77 (d, 7 = 8.6 Hz, 2H), 4.91 (s, 1 ,2, 3 -thiadiazole- 5 -carboxamide 2H); LCMS (M- l): 417.85
4-(((trifluoromethyl)thio)methyl)-N- Ή-NMR (400 MHz, DMSO-i ) δ 11.14 (s, IH), 8.12 (3-((trifluoromethyl)thio)phenyl)- (s, IH), 7.87-7.90 (m, I H), 7.53-7.61 (m, 2H), 4.92 (s, 1 ,2, 3 -thiadiazole- 5 -carboxamide 2H); LCMS (M-l): 417.80
N-(4-(trifluoromethoxy)phenyl)- Ή- MR (400 MHz, DMSO- ) δ 11.08 (s, IH), 7.80 (((trifluoromethyl)thio)methyl)- (dd, 7 = 7.1, 2.2 Hz, 2H), 7.42 (dd, ,/ = 9.0, 0.7 Hz, 2H), 1 ,2,3-thiadiazole-5-carboxamide 4.92 (s, 2H): LCMS (M- l): 401.80
! N-(3-(trifluoromethoxy)phenyl)-' Ή-NMR (400 MHz, DMSO-i¾) δ 11.14 (s, I H), 7 (((trifluoromethyl)thio)methyl)- (s, I H), 7.67 (dd, 7 = 8.1 , 1.0 Hz, IH), 7.54 (t, 7 =
1 ,2, 3 - thiadiazole- 5 -c arboxamide Hz, IH), 7.20 (dt, 7 = 8.3, 1.2 Hz, IH), 4.92 (s, 2
LCMS (M-l): 401.80
N-(2,4-dichlorophenyl)-4- 1R (400 MHz, DMSO- ) δ 10.86 (s, I H), 7.77 (fluoromethyl)- 1 ,2,3-thiadiazole-5 (d, ,/ = 2.3 Hz, I H), 7.68 (d, 7 = 8.6 Hz, IH), 7.51 (dd, carboxamide 7 = 8.6, 2.4 Hz, IH), 5.97 (d, 7 = 47.4 Hz, 2H); LCMS
(M-l): 303.8
! N-(2-fluoro-3 Ή-NMR (400 MHz, DMSO-^) δ 11.13 (s, IH), 8.08
(trifluoromethyl)phenyl)-4 (t, 7 = 7.8 Hz, IH), 7.71 (t, 7 = 6.7 Hz, I H), 7.50 (t, 7 (fluoromethyl) 2,3-thiadiazole-5- = 7.9 Hz, IH), 5.98 (d, 7 = 47.2 Hz, 2H); LCMS carboxamide fM-1): 321.9
4-(fl uorometh yl)-N-(2- Ή-NMR (400 MHz, DMSO- ) δ 10.92 (s, IH), (trifluoromethyl)phenyl)- 1 ,2,3- 7.78-7.86 (m, 2H), 7.59-7.68 (m, 2H), 5.97 (d, 7 thiadiazole-5-carboxamide 47.4 Hz, 2H); LCMS (M-l): 303.8
N-(2-chloro-3- R (400 MHz, DMSO--4 δ 1 1.05 (s, I H), 7.99
(trifl uorometh yl)phen yl)-4- (d, 7 = 8.1 Hz, IH), 7.86 (dd, 7 = 7.9, 1.3 Hz, I H),
(fluoromethyl)- 1 ,2,3-thiadiazole-5 7.64-7.68 (m, I H), 6.01 (d, 7 = 47.4 Hz, 2H); LCMS carboxamide (M-l): 337.9
N-(4-(trifluoromethyl)phenyl)-4- 'H-NMR (400 MHz, DMSO- ) δ 11.22 (s, IH), 7.92
(((trifluoromethyl)thio)methyl)- (d, 7 = 8.6 Hz, 2H), 7.79 (d, 7 = 8.6 Hz, 21 f h 4.92 (s, l,2,3-thiadiazole-5-carboxaniide 2H); LCMS (M-l): 385.85
N-(2-chloro-4- 'H-NMR (400 MHz, DMSO-^) δ 11.10 (s, IH), 8.05 (trifluoromethyl)phenyl)-4- (d, 7 = 1.5 Hz, IH), 7.85-7.92 (m, 2H), 4.94 (s,
(((trifluoronieihyl)thio)methyl)- LCMS (M- l): 419.80
1 ,2, 3 -thiadiazole- 5 -carboxamide
Figure imgf000124_0001
Figure imgf000125_0001
carboxamide 6H); LCMS (M-l): 281.95
N-(3-(trifluoromethoxy)phenyl)-4- 'H-NMR (400 MHz, OMSO-d6) δ 11.17 (s, IH), 7.78 (((trifluoromethyl)sulfinyl)methyl)- (s, IH), 7.65 (dd, J = 8.3, 1 .0 Hz, I H), 7.53 (t, ./ = 8.2 1 ,2, 3 -thiadiazole-5 -carboxamide Hz, IH), 7.18 (dt, J - 8.2, 1.2 Hz, IH), 5.34 (d, J - 13.4
Hz, IH), 5.19 (d, ./ = 13.9 Hz, IH); LCMS (M-l): 417.85
N-(3,5-dicyclopropylphenyl)-4- Ή-NMR (400 MHz, DMSO-4) δ 10.82 (s, I H), 7.61 (difluoromethyl)- 1 ,2,3-thiadiazole-5- (t, J = 52.9 Hz, IH), 7.12 (d, ./ = 1 .7 Hz, 2H), 6.65 (s, carboxamide IH), 1.83-1.89 (m, 2H), 0.90-0.95 (m, 4H), 0.60-0.64
(m, 4j 15: LCMS (M-l ): 333.95
4-(difluoromethyl)-N-(3-fluoro-5- Ή-NMR (400 MHz, DMSQ-i¾) δ 12.66 (s, IH), methylphenyl)- 1 ,2,3-thiadiazole-5- 7.59-7.72 (m, 2H), 7.43 (t, ./ = 52.2 Hz, IH), 7.04 (d, J carbothioamide = 9.5 Hz, IH), 2.35 (s, 3H); LCMS (M-l): 301.85
N-(3-bromo-5-methylphenyl)-4- 1 H-NMR (400 MHz, DMSO-^) δ 12.65 (s, IH), 7.99 (difluoromethyl)- 1 ,2,3-thiadiazoIe-5- (s, IH), 7.48-7.74 (m, 2H), 7.42 (s, IH), 2.35 (s, 3H); carbothioamide LCMS (M-l): 363.75
4-(di fl uorometh yl) - N- (3 , 5 - 1H-NMR (400 MHz, DMSO-i¾ ό 12.47 (s, IH), dimethylphen yl)- 1 ,2, 3 - thiadiazole- 5 - 7.44-7.71 (m, 3H), 6.98 (s, I H), 2.29 (s, 6H); LCMS carbothioamide (M-l): 297.85
N-(3-chloro-5-methylphenyl)-4- Ή-NMR (400 MHz, DMSO-i¾) δ 12.66 (s, I H), 7.87
(difhioromethyl)- 1 ,2,3 -ihiadiazole-5- (s, IH), 7.48-7.74 (m, 2H), 7.28 (s, IH), 2.36 (s, 3H); carbothioamide LCMS (M-l ): 317.85
N-(3-chloro-5-methylphenyI)-4- Ή-NMR (400 MHz, DMSO-d6) δ Ί .56 (t, J = 52.5 Hz, (difluoromethyl)-N-methyl- 1 ,2,3- IH), 7.39 (s, IH), 7.29 (s, IH), 7.21 (s, IH), 3.38 (s, thiadiazole-5-carboxamide 3H), 2.25 (s, 3H); GCMS (M-l): 317.1
N-(3-bromo-5-niethyl.phenyl.)-4- Ή-NMR (400 MHz, DMSO-d6) δ 7.42-7.69 (ni, 3H), (difluoromethyl)-N-methyl- 1 ,2,3- 7.25 (s, IH), 3.38 (s, 3H), 2.24 (s, 3H); GCMS (M-l): thiadiazole-5-carboxamide 363.10
4-(difluoromethyl)-N-(3,5- 'H-NMR (400 MHz, DMSO-J6j δ 7.59 (t, J = 52.9 Hz, dimethylphenyl)-N-methyl- 1 ,2,3 - IH), 7.02 (s, 3H), 3.37 (s, 3H), 2.22 (s, 6H); LCMS thiadiazole-5-carboxamide (M-l): 298.00
4-(difluoromethyl)-N-(3-fluoro-5- * l l-NMR (400 MHz, DMSO-^) δ 7.56 (t, / = 52.7 Hz, methylphenyl)-N-methyl- 1 ,2,3- IH), 7.17 (dd, J = 9.8, 2.0 Hz, I H), 7.08 (d, J = 10.5 thiadiazole-5-carboxamide Hz, 2H), 3.38 (s, 3H), 2.26 (s, 3H); LCMS (M-l):
301 .95
4-(difluoromethyl)-N-(2,5- Ή-NMR-NMR (400 MHz, DMSO- ) ·'> 10.53 (s, dimethylphenyl)- 1 ,2,3 -thiadiazole- 5- I H), 7.66 (t, J = 52.9 Hz, IH), 7.02-7.27 (m, 3H), 2.29 carboxamide (s, 3H), 2.20 (s, 3H); LCMS (M-l ): 281.90
N-(2-bromo-5-methylphenyl)-4- Ή-NMR-NMR (400 MHz, DMSO- ) δ 10.87 (s, (difkioromethyl)- 1 ,2,3 -thiadiazole-5- IH), 7.11-7.77 (m, 3H), 2.32 (s, 3H); LCMS (M-l): carboxamide 347.80
N-(3-aminophenyl)-4- ' H-NMR (400 MHz, DMSO- δ 10.72 (s, I H), 7.62 (difl.uoromethyl)- 1 ,2,3-thiadiazole-5- (i, J = 52.9 Hz, IH), 6.98-7.02 (m, 2H), 6.76 (dd, J = carboxamide 7.9, 1.1 Hz, IH), 6.37 (dt, i = 8.0, 1.0 Hz, I H), 5.23 (s,
2H); LCMS (M-l): 268.85
N-(3-cyclopropylphenyl)-4- 1 H-NMR (400 MHz, OM$0-d6) δ 10.81 (s, IH), 7.44
(fluoromethyl)-l,2,3-thiadiazole-5- (d, J = 8.0 Hz, IH), 7.38 (s, I H), 7.24 (dd, ,/ = 8, 4 Hz, carboxamide IH), 6.89 (d, J = 7.6 Hz, IH), 5.89 (d, J = 47.6 Hz,
2H), 1.88-1.92 (m, IH), 0.93-0.97 (m, 2H), 0.61-0.64 (m, 2H); LCMS (M-l): 275,9
545 N-(3 -bromophenyl)-4- {H-NMR (400 MHz, OMSO-d6) δ 11.06 (s, IH), 8.01
(fluoromethyl)-l,2,3-thiadiazole-5- (d, J = 1 .7 Hz, 1H), 7.62 (id, ./ = 4.5, 2.2 Hz, 1H), carboxamide 7.35-7.40 (m, 2H), 5.97 (d, J = 47.2 Hz, 2H); LCMS •: M ·!· ! ); 315.8
546 4-(fluoromethyl)-N-(4- Ή-NMR (400 MHz, DMSO-i¾) δ 9.50-9.54 (m, I I I ). methoxybenz yl) - 1,2,3- thiadia zole -5 - 7.25-7.28 (m, 2H), 6.90-6.94 (m, 2H), 5.94 (dd, / = carboxamide 47.3, 2.8 Hz, 2H), 4.39-4.43 (m, 2H), 3.73 (s, 3H);
LCMS (M-i): 279.9
547 N-(2-chloro-5-methylphenyl)-4- Ή-NMR-NMR (400 MHz, DM. O- /,·, ) δ 10.86 (s,
(difluoromethyl)- l,2,3-thiadiazole-5- IH), 7.16-7.77 (m, 4H), 2.33 (s, 3H); LCM S (M-l ): carboxamide 301.85
548 4-(difluoromet yl)-N-(2-fluoro-5- Ή-NMR-NMR (400 MHz, DMSO- ) δ 10.91 (s, methylphenyl)- 1 ,2,3-thiadiazole-5- IH), 7.09-7.76 (m, 4H), 2.32 (s, 3H); LCMS (M-i): carbox amide 285.95
549 4-(difluoromethyl)-N-(5,6,7,8- 'H-NMR-NMR (400 MHz, DMSO-^) δ 10.44 (s, tetrahydronaphthalen- 1 -yl)- 1 ,2,3 - IH), 7.65 (t, J - 52.9 Hz, IH), 7.03-7.26 (m, 3H), 2.77 thiadiazole-5-carboxamide (d, J = 5.6 Hz, 2H), 2.63 (d, / = 5.6 Hz, 2H), 1.73 (d, J
= 3.2 Hz, 4H); LCMS (M-l): 307.95
550 4-(difluoromethyl)-N-(l,2,3,4- 1H-NMR-NMR (400 MHz, DMSO-de) δ 9.58 (d, J - tetrahydronaphthalen- 1 -yl)- 1 ,2,3- 8.3 Hz, I H), 7.64 (t, ./ = 53.1 Hz, IH), 7.12-7.31 (rn, thi adiazo 1 e- 5 -carbox amide 4H), 5.19 (m, IH), 2.68-2.83 (m, 2H), 1.72-2.04 (m,
4H); LCMS (M-l): 307.95
551 N-(2-bromo-4-methylphenyl)-4- 'H-NMR-NMR (400 MHz, DMSO- ) δ 10.84 (s, (difluoromethyl)- l,2,3-thiadiazole-5- IH), 7.27-7.76 (m, 4H), 2.26 (s, 3H); LCMS (M-i): carbox amide 345.80
552 N-(2-chloro-5-methoxyphenyl)-4- 'H-NMR-NMR (400 MHz, DMSO-^) δ 10.86 (s,
(difluoromethyl)- l,2,3-thiadiazole-5- IH), 7.47-7.77 (m, 2H), 7.33 (d, / = 2.7 Hz, IH), carboxamide 6.91-6.96 (m, I H), 3.75-3.96 (s, 3H); LCMS (M-l):
317.85
553 N-(3-chloro-2-methylphenyl)-4- Ή- MR-NMR (400 MHz, DMSQ-i¾) δ 10.81 (s, (difluorometliyi)- 1 ,2,3-thiadiazole-5- IH), 7.66 (t, J = 52.9 Hz, IH), 7.28-7.45 (m, 3H), carboxamide 2.23-2.28 (s, 3H); LCMS (M-l ): 301.85
554 4-(difluoromethyl)-N-(2,3-dihydro- ' H-NMR(400 MHz, DMSO-ί ,ί) δ 10.63 (s, IH), 7.65 1 H-inden-4-yl)- 1 ,2,3-thiadiazole-5- (i, J = 52.9 Hz, IH), 7.35 (d, J = 7.3 Hz, IH), 7.14-7.20 carboxamide (m, 2H), 2.87 (di, J = 30.6, 7.5 Hz, 4H), 1.98-2.05 (m,
2H); LCMS (M-l ): 293.9
555 N-(4-chloro-3- Ή-NMR (400 MHz, OM$Q~d6) δ 1 1 . 17 (s, IH), 8.09 (difluoromethyl)phenyl)-4- (d, J - 2.3 Hz, IH), 7.84 (dd, J = 8.8, 2.4 Hz, IH), 7.63 (chloromethyl)- 1 ,2,3-thiadiazole-5- (d, ./ = 8.7 Hz, IH), 7.23 (t, ./ = 54.2 Hz, IH), 5.31 (s, carboxamide 2H); LCMS (M-l):335.8
556 N-(4-chloro-3- Ή-NMR (400 MHz, DMSO- ) δ 12.80 (s, I H), 8.26
(dif luoromethyl )phenyl ) - 4- (s, I H), 8.01 (d, ,/ = 7.9 Hz, IH), 7.49-7.75 (m, 2H),
(difluoromethyl)- 1 ,2,3-thiadiazole-5- 7.26 (t, / = 54.1 Hz, I H); LCM S (M- l ): 353.75 carbothioamide
557 N-(4-chloro-3- Ή-NMR (400 MHz, DMSO-ii6) δ 11.28 (s, I H), 8.07
(dif luoromethyl )phenyl ) - 4- (d, J = 2.4 Hz, 1 H), 7.80 (dd, J = 8.7, 2.4 Hz, 1 H),
(difluoromethyl)- 1 ,2,3-thiadiazole-5- 7.50-7.76 (m, 2H), 7.23 (t, J = 54.2 Hz, IH). LCMS carboxamide (M-l); 337.8 558 I N-(4-chloro-3- 'H-NMR (400 MHz, DMSO-i¾) δ 7.39-7.76 (m, 4H),
(difluoromethyl)phenyl) - 4 - 7.13 (t, 7 = 54.0 Hz, I H), 3.37 (d, 7 = 19.7 Hz, 3H); (difluoromethyl)-N-methyl- 1 ,2,3- GCMS(M)353
thiadiazole-5-carboxamide
559 I N-(3-cyclopropyl-5-methylphenyl)- 'H-NMR (400 MHz, D SO --,/,. ) δ 12.48 (s, IH),
4- (difluoromethyl)- l,2,3-thiadiazole- 7.46-7.73 (m, IH), 7.36-7.41 (m, 2H), 6.90 (d, 7 = 4.6
5- carbothioamide Hz, IH), 2.30 (s, 3H), 1.90- 1 .94 (m, I H), 0.95-1.00
(m, 2H), 0.65-0.68 (m, 2H); LCMS (M-l): 323.9
560 ! N-(4-chloro-3- Ή-NMR (400 MHz, DMSO-t¼) δ 11.15 (s, I H), 8.07
(dif luoromethyl )phenyl ) - 4- (d, 7 = 2.4 Hz, I H), 7.85 (dd, 7 = 8.8, 2.5 Hz, IH), 7.63 (((tri f 1 uorometh yl)thio)methy 1 )- (d, 7 = 8.7 Hz, IH), 7.23 (t, 7 = 54.2 Hz, IH), 4.90 (s, l,2.3-thiadiazole-5-carboxamide 2H); LCMS (M-l ): 401.8
4-(difluoromethy 1 ) - N - methy 1 - N - Ή-NMR (400 MHz, DMSO-ifc) δ 7.70 (t, 7 = 53 (5,6,7,8 - tetrah ydronaphthalen - 1 - y 1 ) IH), 7.19-7.28 ( m. 3H), 3.33 (s, 3H), 2.77 (m, l,2,3-thiadiazole-5-carboxamide 1.62-1.76 (m, 4H); LCMS (M-l): 324.00
562 I 4-(difluoromethyl)- 'H-NMR (400 MHz, CDC13) δ 7.55 (t, 7 = 53.8 Hz, methylphenyl)-N-methyl- 1 ,2,3- IH), 7.32 (dd, 7 = 8.4, 6.0 Hz, I H), 7.16 (id, ./ = 8.2, 2.7 thiadiazole-5-carboxamide Hz, IH), 6.94 (dd, 7 = 8.3, 2.7 Hz, IH), 3.44 (s, 3H),
2.17 (s, 3H); LCMS (M- l): 301.95
N-(5-chloro-2-methylphenyl)-4 Ή-NMR (400 MHz, CDC13) δ 7.40-7.69 (rn, 2H), 7.30 (difluoromethyl)-N-methyl- 1,2, (s, IH), 7.23 (d, 7 = 2.2 Hz, IH), 3.43 (s, 3H), 2.17 (s, thiadiazole-5-carboxamide 3H); LCMS (M-l): 314.00
564 4-(difluoromethyl)-N- Ή-NMR (400 MHz, DMSO-^) δ 7.68 (t, J = 53.0 Hz, dimethylphenyl)-N-methyl- 1 , I H), 7.23-7.27 (m, 3H), 2,26 (s, 3H), 2.08 (s, 3H); thiadiazole-5-carboxamide LCMS (M+l): 298.00
4-(difluoromethyl)-N-methyl-N-( Ή-NMR (400 MHz, CDC13) δ 7.61 (d, J = 53.7 Hz, tolyl)- 1 ,2,3-thiadiazole-5- IH), 7.45 (id, 7 = 7.6, 1.2 Hz, I H), 7.32-7.37 (m, 2H), carboxamide 7.17-7.19 (m, I H), 3.44 (s, 3H), 2.20 (s, 3H); LCMS
(M+l): 284.05
566 ! 4-(difluoromethyl)-N-methy]-N-(2- ¾-NMR (400 MHz, CDCI3) δ 7.39-7.68 (m, 4H), 3.47 methyl- 5 - (trifluoromethy l)phenyl) - (s, 3H), 2.28 (s, 3H); LCMS (M-l): 349.6
l,2,3-thiadiazole-5-carboxamide
4-(difluoromethyl)-N-(2-fluoro-5- : (400 MHz, DMSO-ii6) δ 7.41 -7.69 (m, 2H), methylphenyl)-N-methyl- 1 ,2,3- 7.17-7.27 (m, 2H), 3.37 (s, 3H), 2.26 (s, 3H); LCMS thiadiazole-5-carbox amide l): 301 .95
568 ! N-(3-chloro-2-methylphenyl)-4- Ή-NMR (400 MHz, CDC13) δ 7.40-7.67 (m, 2H), (difluoromethyl)-N-methyl- 1 ,2,3- 7.1 1 -7.26 (m, 2H), 3.44 (s, 3H), 2.26 (s, 3H); LCMS thiadiazole-5-carboxamide (M+l): 318.0
569 ! N-(2-bromo-4-methylphenyl.)-4- ¾-NMR (400 MHz, DMSO-d6) δ 7 '.63-7. ,76 (m, IH), (difluoromethyl)-N-methyl- 1 ,2,3- 7.49-7.58 (m, I H), 7.34 (dt, 7 = 8.1, 1 .0 Hz, IH), 3.31 thiadiazole-5-carboxamide (s. 3H), 2.35 (s, 3H); LCMS (M+2): 363.8
4-(difluoromethyl)-N-(2- ¾-NMR (400 MHz, DMSO- ) δ 10.46 (s, IH), 7.80 methoxyphenyl)- 1 ,2,3-thiadiazole-5- (d, 7 = 7.8 Hz, I H), 7.61 (t, 7 = 52.9 Hz, I H), 7.25 (t, 7 carboxamide = 7.6 Hz, I H), 7.13 (d, 7 = 8.1 Hz, IH), 7.00 (id, 7 =
7.6, 1.3 Hz, IH), 3.83 (s, 3H); LCMS (M-l): 283.9
571 ! 4-(difluoromethyl)-N-(2-methoxy-5- Ή-NMR (400 MHz, DMSO- ') δ 10.40 (s, IH), methylphenyl .)- 1 ,2,3-thiadiazole-5- 7.48-7.74 (m, 2H), 7.03 (m, 2H), 3.79 (s, 3H), 2.27 (s, carboxamide 3H); LCMS (M+l): 300.00
N-(4-bromonaphthalen- 1 -yl)-4- Ή-NMR (400 MHz, DM . SO ·· /,, } δ 11.20 (s, IH), (difluoromethyl)- 1 ,2,3-thiadiazole-5 8.16-8.22 (m, 2H), 7.99 (d, 7 = 8.1 Hz, I H), 7.57-7.83 carboxamide (m, 4H); LCMS (M-l): 381.8 4- (difluoromethyl)-N-(3- 1H-NMR (400 MHz, DMSO-rfi) δ 10.96 (s, IH), 7.63 isopropoxyphenyl)- 1 ,2,3 -thiadiazole- 0, J = 52.8 Hz, IH), 7.26-7.33 (m, 2H), 7.18 (d, J = 8.8
5 - carbo amide Hz, I H), 6.74-6.76 (m, I H), 4.54-4.60 (m, I H),
1.24-1.29 (m, 6H); LCMS (M-l): 311.9
4-(difluoromethyl)-N-(6- 1 H-NMR (400 MHz, OMSO-d6) δ 11.65 (s, I H), 7.94 metliylpyridin-2-yl)- 1 ,2,3 - (d, 7 = 7.1 Hz, IH), 7.49-7.80 (m, 2H), 7.11 (d, J = 7.6 thiadiazole-5 -carboxamide Hz, IH), 2.44 (s, 3H); LCMS (M+l): 271.0
4-(difluoromethyl)-N-(3-fluoro-4- ' H-NMR (400 MHz, CDC33) δ 7.44 (d, J = 53.9 Hz, methylphen yl)-N-methyl- 1 ,2,3- IH), 7.17-7.24 (m, IH), 6.83-6.87 (m, 2H), 3.47 (s, thiadiazole-5 -carboxamide 3H), 2.29 i d. ./ - 1 .4 Hz, 3H); LCMS (M+l): 301.0
4 - (difluoromethy 1 j - N -methyl- N - ( 4- ' H-NMR (400 MHz, CDC13) δ 7.31 -7.50 (m, 2H), meth yl - 3 - (trifluoromethy l)phenyl) - 7.20-7.23 (m, 2H), 3.52 (s, 3H), 2.52 (d, ,/ = 1.2 Hz, l,2,3-thiadiazole-5-carboxamide 3H); LCMS (M+l ): 351.9
4-(difluoromethyl)-N-(4-fluoro-3- 'H-NMR (400 MHz, CDC13) δ 7.50 (d, ./ - 54.0 Hz, methylphenyl)-N-methyl- 1 ,2,3- IH), 6.98-7.08 (m, 3H), 3.48 (s, 3H), 2.28 (d, / = 2.0 thiadiazole-5-carboxamide Hz, 3H); LCMS (M+l): 302.0
4-(difluoromethyl)-N-(3- 'H-NMR (400 MHz, CDC13) δ 7.31-7.58 (m, 2H), 6.94 isopropoxyphenyl)-N-methyl- 1 ,2,3- (dd, J = 8.4, 1.8 Hz, IH), 6.67-6.74 (m, 2H), 4.48-4.54 thiadiazole-5-carboxamide (m, I H), 3.47 (s, 3H), 1.28-1.36 (m, 6H); LCMS
(M+l ): 328.0
4-(difluoromethyl)-N-(2-methoxy-5- 'H-NMR (400 MHz, CDC13) δ 7.45 ((, J = 53 H/, methylphenyl)-N-methyl- 1 ,2,3- IH), 7.19 (dd, J = 8.4, 1.6 Hz, IH), 7.01 (d, J = 2.0 Hz, thiadiazole-5-carboxamide IH), 6.81 (d, J - 8.3 Hz, IH), 3.75 (s, 3H), 3.40 (s, 3H),
2.30 (s, 3H); LCMS (M+l): 314.0
N-(4-bromonaphthalen- 1 -yl)-4- 1 H-NMR (400 MHz, CDC13) δ 8.36-8.38 (m, IH), (difluoromethyl)-N-methyl- 1 ,2,3- 7.49-7.84 (m, 5H), 7.33 (m, IH), 3.62 (s, 3H); LCMS thi adiazo 1 e-5 - carbox amide (M+l): 399.8
4-(difluoromethyl)-N-(2- 'H-NMR (400 MHz, CDCI3) δ 7.38-7.43 (m, IH), 7.28 methoxyphenyl)-N-methyl- 1 ,2,3 - (s, IH), 7.21 (dd, / = 7.7, 1.6 Hz, IH), 7.01 (td, / = 7.7, thi adiazo 1 e- 5 -carbox amide 1.2 Hz, IH), 6.92 (dd, J = 8.4, 1.1 Hz, I H), 3.79 (s,
3H), 3.41 (s, 3H); LCMS (M-l ): 299.9
N-(4-bromo-2,5-dimethylphenyl)-4- H-NMR (400 MHz, DMSO- ) δ 7.62(3H), 3.36(3H), (difluoromethyl)-N-methyl- 1 ,2,3- 2.38(6H); GCMS(M) 377.
thiadiazole-5-carboxamide
N-(4-chloro-3- 'H-NMR (400 MHz, DM Si )···<·. , ) δ 11.47-1 1.14 (I H), (fltioromethyl)phenyl)-4- 7.97-7.88 (IH), 7.82-7.64 (2H), 7.62-7.54 (IH), (dif uoromethyl)- l,2,3-thiadiazole-5- 5.73-5.56 (I H), 5.54-5.47 (I H); LCMS (M-l): 319.8 carboxamide
N-(2-bromo-4-chloro-5- 'H-NMR (400 MHz, DM Si )···<·. , ) δ 11.24-10.99 (I H), (dif luoromethyl )phenyl ) - 4- 8.32(2H), 7.5 (s, IH); LCMS (M-l): 435.7
(trifluoromethyl)- 1 ,2,3-thiadiazole-5- carboxamide
N-(2-bromo-4-chloro-5- 'H-NMR (400 MHz, DMSO-,/,, ) .) 11.16 (I H), 8.18 (s, (dif luoromethyl )phenyl ) - 4- I H), 7.78(s, I H), 7.54 (s, IH), 7.29(s, IH); LCMS (difluoromethyl)- 1 ,2,3-thiadiazole-5- (M-l): 417.6
carboxamide
4 -{dill uorometh yl) -N- (2 , 6- 'H-NMR (400 MHz, DMSO-ifc) δ 10.54 (s, I H), 7.66 dimethylphenyl)- 1 ,2,3 -thiadiazole- -5- (t, J - 53.2 Hz, IH), 7.12-7.19 (m, 3H), 2.22 (s, 6H); carboxamide LCMS (M-l ): 281.9
Figure imgf000130_0001
603 N-(3-bromo-5-methylphenyl)-4- 1H-NMR (400 MHz, DMSO-rfi) δ 10.93 (s, IH), 7.77 ( ( (trifluoromethy 1) thi o)methyl) - (s, I H), 7.45 (s, I H), 7.23 (s, IH), 4.89 (s, 2H), 2.31 (s, l,2,3-thiadiazole-5-carboxamide 3H); LCMS (M-l): 41 1.7
604 N-(3-fluoro-5-methylphenyl)-4- 'H-NMR (400 MHz, DMSO-rfi) δ 10.97 (s, IH), 7.40 ( ( (trifluoromethy 1) thi o)methyl) - (d, J = 1 1.0 Hz, IH), 7.29 (s, I H), 6.86 (d, J = 9.8 Hz, 1,2,3 -thiadiazole-5 -carboxamide I H), 4.89 (s, 2H), 2.32 (s, 3H); LCMS (M- l): 349.8
605 N-(3 ,5-dimethylphenyl) -4- Ή-NMR (400 MHz, DMSO-ί ,ί) δ 10.75 (s, IH), 7.31
( ( (trifluoromethy 1 ) thi o)m ethyl) - (s, 21 i s. 6.84 (s, IH). 4.90 (s. 2H), 2.28 (s. 6H); LCMS 1 ,2, 3 -thiadiazole-5 -carboxamide (M-l ): 345.9
606 4-(difluoromethyl)-N-(2- Ή-NMR (400 MHz, DMSO-i¾) 0 7.18-7.74 (m, 6H), fluorobenzyl)-N-methyl- 1 ,2,3- 4.61 (d, J = 112.0 Hz, 2H), 2.88 (d, J = 75.3 Hz, 3H); thiadiazole-5-carboxamide LCMS (M-l): 300.1
607 4-(difluoromethyl)-N-(5- Ή-NMR (400 MHz, DMSO-i/6) δ 11.61 (s, IH), 8.24 methylpyridin-2-yl)- 1 ,2,3- (s, I H), 8.02 (d, ./ = 8.1 Hz, IH), 7.49-7.76 (m, 2H), thiadiazole-5-carboxamide 2.30 (s, 3H); LCMS (M+l): 270.9
608 N-(4-chloro-3~ 1H-NMR (400 MHz, DMSO-rf6) δ 11.29(1H), (difluoromethyi)phenyi)-4- 8. 15( 1 1 3 }. 7.85 (IH), 7.66 (IH), 7.26(1 H), 6.05 (I H), (fluoromethyl)- 1 ,2,3-thiadiazole-5- 5.91(1H); LCMS (M-l): 319.8
carboxamide
609 4 - (difl uorometh yl) -N- (2 , 6- 1H-NMR (400 MHz, DMSG-i¾) δ 7.77 (t, J = 53.2 Hz, dimethylphenyl)-N-methyl- 1 ,2,3- IH), 7.40-7.44 (m, I H), 7.30 (dd, J = 7.6, 0.5 Hz, 2H), thiadiazole-5-carboxamide 3.32 (s, 3H), 2.13 (s, 6H); LCMS (M-l ): 297.9
610 N-(4-bromo-3-methylphenyl)-4- Ή-NMR (400 MHz, DMSO-ii6) δ 7.41 -7.68 (m, 3H), (difl uorometh y 1 )-N-methy 1 - 1 ,2,3 - 7.14 (d, J = 7.3 Hz, IH), 3.36 (s, 3H), 2.29 (s, 3H); thiadiazole-5 -carboxamide LCMS (M-l ): 359.9
611 4- (chloromethyl)-N- (3,5- Ή-NMR (400 MHz, DMSO~d6) δ 7,62 (d, J = 12 Hz, dichlorophenyl.)-N-methyl - 1 ,2,3- 3H), 4.88 (s, 2H), 3.35 (s, 3H); LCMS (M-l): 333.9 thiadiazole-5-carboxamide
612 4- (difluoromethyl)-N-(4- Ή-NMR (400 MHz, DMSO-i¾) δ 13.67 (s, I H), 7.87 ethylthiazol-2-yl)- 1 ,2,3-thiadiazole- (t, / = 53.2 Hz, I H), 6.85 (s, IH), 2.61 (q, J = 7.5 Hz,
5- carboxamide 2H), 1.19 (t J = 7.6 Hz, 3H); LCMS (M-l ): 288.8
613 N-(4'-chloro-5 -methyl- [ 1 , Γ- ' H-NMR(400 MHz, DM SO- ) S 11.06 (s, I H), biphenyl]-3-yl)-4-(difluoromethyl)- 7.52-7.79 (m, 7H), 7.33 (s, IH), 2.40 (s, 3H); LCMS l,2,3-thiadiazole-5-carboxamide (M-l): 378.5
614 N-(3',4'-dichloro-5-methyl-[ l, - : ! l-KMR( 4( i MHz, DMSO-i/6) δ 1 1.07 (s, IH), 7.88 biphenyl]-3-yl)-4-(difluoromethyl)- (d, J = 2.2 Hz, I H), 7.53-7.79 (m, 5H), 7.40 (s, IH), l,2,3-thiadiazole-5-carboxamide 2.40 (s, 3H); LCMS (M-l ): 412.0
615 5-(4-chiorophenyl)-4,5-dihydro-6H- XH-NMR (400 MHz, CDC13) δ 7.70-7.73 (m, 2H), pyrrolo [3 ,4-d] [ 1 ,2,3 ] thiadiazol-6-one 7.42-7.46 (m, 2H), 5.21 (s, 2H); GCMS: 251
616 5-(4-(trifluoromethoxy)phenyl)-4,5- Ή-NMR (400 MHz, DMSO-^) δ 7.97 (dd, J = 6.9, dihydro-6H-pyrrolo[3,4- 2.3 Hz, 2H), 7.50 (dd. J = 9.2, 0 8 Hz, 2H), 5.49 ( s, d] [ 1 ,2,3] thiadiazol-6-one 2H); GCMS: 301
617 5-(3-(trifluoromethoxy)phenyl)-4,5- 'H-NMR (400 MHz, DMSO-i¾) δ 8.02 (s, IH), dihydro-6H -pyrroio [3,4- 7.80-7.83 (m, IH), 7.62 (t, J = 8.3 Hz, IH), Ί .25-1.21 d] [ 1 ,2,3]thiadiaz.ol-6-one (m, IH), 5.50 (s, 2H); GCMS: 301
618 5-(3-((trifluoromethyl)thio)phenyl)- 1H-NMR (400 MHz, DMSO--i¾) δ 8.36 (t, J = 1.8 Hz,
4,5-dihydro-6H-pyrrolo[3,4- IH). 7.99 (dq, ./ - 8.2, 1.1 Hz, I H). 7.66 (t. ,/ - 7.9 Hz, d] [ 1 ,2,3] thiadiazol-6-one IH), 7.60 (d, J - 7.8 Hz, IH), 5.52 (s, 2H); GCMS : 317 5-(4-((lrifluoromethyl)thio)phenyl) 'H-NMR (400 MHz, DMSO-<¾) δ 8.02-8.05 (m, 4,5 -dihydro-6H-pyrrolo[3 ,4- 2H), 7.83 (d, / = 8.9 Hz, 2H), 5.52 (s, 2H); GCMS: d] [ 1 ,2,3"|thiadiaz.ol-6-one 316.90
5-(3-chlorophenyl)-4,5-dihydro-6H- Ή-NMR (400 MHz, DMSO-i¾) δ 8.00 (t, J = 2.1 Hz, pyrrolo[3,4-d] [l,2,3]thiadiazol-6-one 1H), 7.81 (ddd, / = 8.3, 2.2, 0.8 Hz, IH), 7.51 (t, J = 8.2
Hz, IH), 7.32 (dq, J = 8.0, 0.9 Hz, I H), 5.49 (s, GCMS: 250.9
5-(3-(trifluoromethyl)phenyl)-4, {H-NMR (400 MHz, DMSO-,/,, ) δ 8.30 (s, IH), 8.09 dihydro-6H-pyrrolo [3,4- (dd, J = 8.3, 1.5 Hz, IH), 7.73 (t, J = 8.0 Hz, IH), 7.61 d] [ 1 ,2,3 "|thiadiaz.ol-6-one (d, J = 7.8 Hz, IH), 5.55 (s, 2H)
5-(4-((difluoromethyl)thio)phenyl) {H-NMR (400 MHz, DMSO-<¾) δ 7.94-7.97 (m, 4,5 -dihydro-6H-pyrrolo[3 ,4- 2H), 7.69 (d, ./ 8.7 Hz, 2H), 7.47 (t, ./ = 55.9 Hz, IH), d] [ 1 ,2,3 jthiad azoi-6-one 5.50 (s, 2H); GCMS: 299
623 I 5-(3,5-dichlorophenyl)-4,5-dihydro- Ή-NMR (400 MHz, DMSO- ) S 7.98 (d, J = 1.8 6H-pyrrolo[3,4-d] [l',2,3]thiadiazol-( Hz, 2H), 7.51 (t, J = 1.8 Hz, IH), 5.50 (s, 2H); GCMS: one 284.90
624 I 5-(3-(trifluoromethoxy)phenyl)-6,7 NMR (400 MHz, DMSO-t¾) δ 7.59 (s, J = 8.1 Hz dihydro-[ 1 ,2,3]thiadiazolo[5,4- , 7.48 (m, 2H), 7.33 (s, J = 8.3 Hz, IH), 4.21 (s, J = c]pyridin-4(5H)-one 5 Hz, 2H), 3.60 (s, ./ = 6.9 Hz, 2H); GCMS(M) 315
5 - ( 3 - ( trifluoromethy 1 )p heny ] ) - 6 , 7 (400 MHz, DMSO-titf) δ 7.84 (s, IH), dihydro-[ 1 ,2,3]thiadiazolo[5,4- 7.74-7.76 (m, I H), 7.67-7.72 (m, 2H), 4.24 (s, ,/ = 6.8 c]pyridin-4(5H)-one Hz, 2H), 3.60-3.63 (m, 2H); GCMS(M) 299
5-(3-(pentafluoro-16- {H-NMR (400 MHz, DMSO-^) δ 8.03 (t, J sulfaneyl)phenyl)-6,7-dihydro- IH), 7.85-7.88 (m, IH), 7.71-7.76 (m, 2H), 4
[ 1 ,2,3]thiadiazolo[5,4-c]pyridin- 6.9 Hz, 2H), 3.62 (t, J = 6.9 Hz, 2H).
4(5H)-one
627 I 5-(4-(trifluoromethyl)phenyl)-6,7 {H-NMR (400 MHz, CDC13) δ 7.72 (
dihydro-[ 1 ,2,3]thiadiazolo[5,4- 2H), 7.50 (s, / = 8.3 Hz, 2H), 4.25 (s, /
c]pyridin-4(5H)-one 3.67 (s, J " = 6.8 Hz, 2H); GCMS(M) 357
628 I 7-bromo-[ l,2,3]thiadiazolo[5,4- {H-NMR (400 MHz, DMSO-i¾) δ 12.59(s, lH), c] pyridin -4( 5 H) -one 7.97(s,lH); LCMS (M-l): 231.75
5-(4-(trifluoromethyl)phenyl)- {H-NMR (400 MHz, CDC13) ( ) 8.03(21 1 ). 7.64(2( 1 i.
[ 1 ,2,3]thiadiazolo[5,4-c]pyridin- 7.50 (2H); GCMS(M) 299
4(5H)-one
630 ! 5-(3-( l,l,2,2- (400 MHz, CDCI3) δ 7.45-7.52 (m, IH), tetrafluoroethoxy)phenyl)-6,7- 7.30-7.32 (m, IH), 7.26-7.24 (m,! H), 7.18-7.21 (m, dihydro- [1 ,2,3] thiadiazolo [5,4■ IH). 5.92 (s, J = 53.0, 2.8 Hz, IH), 4.22 (s. ,/ = 6.8 Hz, c]pyridin-4(5H)-one 2H), 3.66 (s, 2H); GCMS(M) 347
631 ! 4-(difluoromethyl)-N-methyl-N-(2- Ή-NMR (400 MHz, CDC13) δ 7.64-7.74 (m, 2H), ( trifluoromethy 1 )benzyl)- 1 ,2,3- 7.50 (dd, J = 12.3, 7.9 Hz, 3H). 7.25 (m, IH), 5.04 (s, thiadiazole-5-carboxamide 2H), 2.83 (s, 3H); LCMS (M+l): 352.0
4-(difluoromethyl)-N-(3- IH-NMR (400 MHz, DMSO-i¾) δ 7.38-7.79 (m, 2H), fluorobenzyl)-N-methyl- 1 ,2, 7.06-7.23 (m, 3H), 4.57 (s, 2H), 2.87 (s, 3H); LCMS thiadiazole-5-carboxamide (M+l ): 302.2
633 ! N-(2-chlorobenzyl)-4- Ή-NMR (400 MHz, DMSO -Y/,, ) δ 7.35-7.69 (m, 5H),
(difluoromethyi)-N-methyi- 1 ,2,3- 4.81 (s, 2H), 2.50-2.52 (s, 3H); LCMS (M-l): 318.0 thiadiazole-5-carboxamide
634 I N-(3,5-difluorobenzyl)-4- ¾-NMR (400 MHz, CDC13) δ 7.18-7.46 (m, IH),
(difluoromethyl)-N-methyl- 1 ,2,3- 6.90 (d, J = 2.3 Hz, 2H), 6.82 (d, ./ = 2.3 Hz, I H), 4.77 thiadiazole-5-carboxamide (s, 2H), 2.86 (s, 3H); LCMS (M-l ): 317.9 635 4-(difluoromethyl)-N-(2,5- 1H-NMR (400 MHz, CDC13) δ 7,32-7.46 (m, 1H), dimethylbenzyl)-N-methyl- 1 ,2,3- 6.86-7.19 (m, 3! 15. 4,58 (s, 2H), 2.98 (s, 3H), 2.36 (s, thiadiazole-5-carboxamide 3H),2.32 (s, 3H); LCMS (M-l): 310.9
636 4-(difluoromethyl)-N-(3- 'H-NMR (400 MHz, DMSO-i¾) δ 7.57-7.86 (m, 1H),
(((rifluoromethyl)thio)phenyl)- 1 ,2,3- 7.50 (t, J = 7.8 Hz, 1H), 7.38 (d, J = 7.6 Hz, 1H), 7.30 thiadiazole-5-carboximidamide (s, 1H), 7.13-7.26 (m, 3H); LCMS (M- l): 352.80
637 4-(difluoromethyl)-N-(3- ¾-NMR (400 MHz, DMSO- ) δ 7.74 (t, J - 52.7 Hz, (trifluoromethyl)phenyl)- 1 ,2,3- 1H), 7.55 (t, ,/ = 7.9 Hz, IH), 7.38 (d, ./ - 7.6 Hz, 1H), thiadiazole-5-carboximidamide 7.29 (s, IH), 7.13-7.23 (m, 3H); LCMS (M- l ): 320.90
638 4-(difluoromethyl)-N-(3- ' H-NMR (400 MHz, DMSO- ) δ 7.75 (t, ./ = 52.7 Hz,
(pentafluoro-16-sulfaneyl)phenyl)- IH), 7.49-7.58 (m, 2H), 7.45 (s, IH), 7.21-7.36 (rn, l,2,3-thiadiazole-5-carboximidamide 3H); LCMS (M- l): 378.90
639 4-(difluoromethyl)-N-(3- 1 H-NMR (400 MHz, DMSO-i¾) δ 1 '.70 (L J = 52.8 Hz, fluorophenyl)- 1 ,2,3-thiadiazole-5- I H), 7.33-7.38 (m, I H), 7.14 (s, 2H), 6.83-6.88 (m, carboximidamide IH), 6.76-6.81 (m, 2H); LCMS (M- l): 270.85
640 N-(3 -bromo phenyl )-4- 'H-NMR (400 MHz, OMSO-d6) δ 7.70 (t, / = 52.8 Hz, (difluoromethyi)- 1 ,2,3-thiadiazole-5- IH), 7.29 (t, J = 7.9 Hz, IH), 7.21-7.23 (m, IH), 7.17 carboximidamide (t, J = 1.8 Hz, 3H), 6.92-6.94 (m, IH); LCMS (M- l):
33? 7
* Compound names generated using Chemdraw Professional 16.0
As described herein the compounds of formula (I) shows an extremely high fungicidal activity which is exerted with respect to numerous phytopathogenic fungi which attack on important agricultural crops. Compounds of the present invention were also showing promising activity against nematodes and bacterial diseases. Compounds of the present invention were assessed for their activity against one or more of the folio wing fungal diseases and nematodes.
Biological Test Examples (IN VITRO TEST)
Example 1: Pyricularia oryztae (Rice blast):
Compounds were dissolved in 0.3% DMSO and then added to Potato Dextrose Agar medium just prior to dispensing it into Petri dishes. 5ml medium with compound in the desired concentration was dispensed into 60mm sterile petri-plates. After solidification each plate was seeded with a 5mm size mycelial disc taken from the periphery of actively growing virulent culture plates. Plates were incubated in growth chambers at 25°C temperature and 60% relative humidity for seven days and radial growth was measured. Compounds, I 2 3
4 5 6 9 10 1 1 12 14 15 16 17 18
19 20 21 22 23 24 25 26 27 28 29 30
31 32 33 35 36 37 38 39 40 41 42 43
44 45 46 47 48 49 51 52 53 54 56 58
64 65 66 67 68 69 70 71 72 73 74 75
76 77 78 79 80 81 82 84 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100
101 102 103 104 105 106 107 108 109 110 111 112
1 13 1 14 115 116 1 17 1 18 119 120 121 122 123 124
125 126 127 128 129 130 131 132 133 134 135 136
137 138 139 141 142 143 144 145 146 147 148 149
150 151 152 153 154 155 156 157 158 160 161 162
163 164 165 166 167 168 169 170 171 172 173 174
175 176 177 178 179 180 181 183 184 185 186 187
188 189 190 191 192 195 196 198 199 201 202 203
204 205 206 207 208 209 210 211 212 213 214 215
216 217 218 219 220 221 222 223 224 228 229 236
238 244 245 246 247 249 250 255 263 264 267 268
270 271 z. ι 273 274 277 278 279 280 281 282 283
284 285 286 287 288 289 290 291 292 293 294 297
299 300 301 302 303 304 305 306 307 308 309 310
312 313 315 316 317 318 319 320 322 323 324 325
326 327 328 329 331 332 333 336 337 338 339 340
341 342 343 345 346 347 348 349 350 351 352 353
354 355 356 357 358 359 360 361 363 364 365 366
370 371 373 374 375 376 377 379 380 382 383 384
386 387 388 389 390 391 393 394 395 396 397 398
399 400 401 402 404 409 410 413 415 416 419 420
422 423 424 425 426 427 428 429 430 432 433 435
437 438 439 440 446 447 448 449 450 451 452 453
462 466 467 468 469 470 471 472 473 474 476 484
486 488 489 490 491 492 494 497 498 499 500 501
502 503 504 505 507 508 510 51 1 512 513 514 516
517 518 519 521 522 523 524 525 526 527 528 532
533 534 535 536 541 545 548 552 555 556 557 558
559 560 562 563 566 568 573 583 584 585 587 589
590 591 592 593 594 597 599 601 604 606 607 608
615 617 620 621 622 623 624 630 631 632 633 at 300 ppm gave more than 70% control in these tests when compared to the untreated check which showed extensive disease development Example 2: Rhizoctoma solani (Rice sheath blight/Potato black scurf):
Compounds were dissolved in 0,3% DMSO and then added to Potato Dextrose Agar medium just prior to dispensing it into Petri dishes. 5ml medium with compound in the desired concentration was dispensed into 60mm sterile petri-plates. After solidification each plate was seeded with a 5mm size mycelial disc taken from the periphery of actively growing virulent culture plates. Plates were incubated in growth chambers at 25°C temperature and 60% relative humidity for seven days and radial growth was measured. Compounds, 1 2 3
4 5 6 14 15 18 19 20 22 23 24 25
26 27 28 29 31 37 40 41 42 43 44 45
46 47 48 49 51 52 54 56 58 65 66 67
68 69 70 73 74 75 76 77 78 80 81 82
85 87 88 90 92 95 96 97 99 100 101 102
103 104 105 106 107 108 109 110 111 113 114 115
116 117 1 18 120 121 122 123 124 125 126 127 128
129 130 132 133 134 135 136 138 141 142 143 144
145 146 147 148 149 151 153 154 155 156 157 158
160 161 164 165 166 167 168 169 170 171 172 173
174 177 178 179 181 183 184 185 187 188 189 190
191 199 201 202 203 205 206 207 208 209 210 21 1
214 217 218 219 222 223 224 236 244 245 247 249
263 267 268 270 277 278 280 281 282 283 284 285
286 287 288 289 291 292 293 300 301 302 303 304
305 306 307 308 309 310 312 313 315 318 320 322
323 324 325 326 327 328 329 331 332 333 336 337
338 339 342 343 345 346 347 348 349 350 351 352
353 354 356 357 358 359 360 364 365 366 371 374
375 379 380 382 383 386 387 388 389 390 391 393
394 395 396 397 398 399 400 401 404 410 415 416
419 420 431 432 435 453 466 467 469 470 471 472
473 474 476 486 488 489 490 497 498 502 503 504
507 508 510 512 513 519 521 523 524 525 526 527
528 533 535 545 556 557 585 590 591 592 601 602
608 at 300 ppm gav 'e more than 70% control in ihes e tests when compared to untreated check which showed extensive disease development. Example 3: Botr tis cinere (Gray mold):
Compounds were dissolved in 0.3% DMSO and then added to Potato Dextrose Agar medium just prior to dispensing it into Petri dishes. 5ml medium with compound in the desired concentration was dispensed into 60mm sterile petri-plates. After solidification each plate was seeded with a 5mm size mycelial disc taken from the periphery of actively growing virulent culture plates. Plates were incubated in growth chambers at 22°C temperature and 90% relative humidity for seven days and radial growth was measured. Compounds, 1 2 3
4 5 6 11 14 15 16 17 18 19 20 21
22 23 24 25 26 27 28 29 31 33 35 37
40 41 42 43 44 45 46 47 48 49 51 52
54 58 64 65 66 67 68 69 70 74 75
76 77 79 80 81 82 85 86 87 88 92 95
96 97 99 100 101 102 103 104 105 106 107 108
109 110 1 11 1 13 114 115 1 16 117 118 120 121 122
123 124 125 126 127 128 129 130 132 133 134 135
136 138 141 142 143 144 145 147 148 149 151 153
154 155 156 157 158 160 161 162 164 165 166 167
168 169 170 172 174 175 177 178 179 180 181 183
184 185 186 187 188 189 190 191 196 199 201 202
205 206 207 208 209 210 214 217 218 219 222 223
224 235 244 245 247 249 263 264 273 274 278 280
281 282 283 284 285 286 287 288 289 290 291 292
293 300 301 302 303 304 305 306 307 308 309 310
312 313 315 320 322 323 324 325 326 328 329 331
332 „">.)j 336 337 338 339 341 342 343 345 346 347
349 350 351 352 353 354 356 358 359 360 363 364
365 366 371 374 375 377 379 380 382 383 386 387
389 390 391 393 394 395 396 397 398 400 401 404
410 413 414 415 416 419 420 449 452 453 462 466
467 468 469 470 471 472 473 474 476 484 486 488
489 490 492 497 498 502 503 504 507 508 510 511
512 513 515 517 518 519 521 523 524 525 526 527
532 533 534 535 536 544 545 556 557 559 560 572
584 585 590 592 601 604 608 615 623 627 629 630 300ppm gave more than 70% control in these tests when compared to the untreated check which showed extensive disease development.
Example 4t Alternaria solani (Early blight of tomato/potato):
Compounds were dissolved in 0.3% DMSO and then added to Potato Dextrose Agar medium just prior to dispensing it into Petri dishes. 5ml medium with compound in the desired concentration was dispensed into 60mm sterile petri-plates. After solidification each plate was seeded with a 5mm size mycelial disc taken from the periphery of actively growing virulent culture plates. Plates were incubated in growth chambers at 25°C temperature and 60% relative humidity for seven days and radial growth was measured. Compounds 1 2 3
4 5 6 11 13 14 15 17 18 19 21 22
23 24 25 26 77 28 29 30 33 35 37 39
40 41 42 43 44 45 46 47 48 49 51 52
54 56 58 65 66 68 69 70 73 74 75 76
78 79 80 81 82 85 87 88 92 95 97 99
100 101 102 103 104 105 106 107 108 109 110 111
113 114 115 116 118 120 121 1 n 123 124 125 126
127 128 129 130 131 132 133 134 135 136 137 138
141 142 143 144 145 146 147 148 149 151 153 154
155 156 157 158 160 161 162 164 165 166 167 168
169 170 171 172 174 176 177 178 179 180 181 183
184 185 186 187 188 190 191 192 196 199 201 202
205 206 207 208 210 211 214 217 218 219 222 223
224 229 236 244 245 247 249 263 266 267 270 272
273 278 279 280 281 282 283 284 285 286 288 289
290 291 292 293 299 300 301 302 303 304 305 306
307 308 309 310 311 312 313 315 316 318 319 320
322 323 324 325 326 327 328 329 331 332 333 336
337 338 339 341 342 343 345 346 347 348 349 350
351 352 353 354 356 358 359 360 361 363 364 365
366 371 374 375 379 380 382 383 386 387 388 389
390 391 393 394 395 396 397 398 399 400 401 402
404 413 415 416 419 420 421 428 429 432 435 440
452 453 457 466 467 468 469 470 471 472 473 474
484 486 487 488 489 490 492 494 497 498 500 501 502 503 504 507 508 510 512 513 517 519 521 523
524 526 527 528 533 534 535 536 545 552 556
557 559 584 585 592 597 599 601 604 608 611 612
613 616 at 300 ppm gave more than 70% control in these tests when compared to the untreated check which showed extensive disease development.
Example 5: Colletotrichum capsici (anthracnose):
Compounds were dissolved in 0.3% DMSO and then added to Potato Dextrose Agar medium just prior to dispensing it into Petri dishes. 5ml medium with compound in the desired concentration was dispensed into 60mm sterile petri-plates. After solidification each plate was seeded with a 5mm size mycelial disc taken from the periphery of actively growing virulent culture plates. Plates were incubated in growth chambers at 25°C temperature and 60% relative humidity for seven days and radial growth was measured. Compounds 1 2 3
4 5 6 1 1 12 13 14 15 16 17 18 19
20 21 22 23 24 25 26 27 28 29 30 33
35 36 37 40 41 44 45 46 47 48 49 51
52 54 56 58 65 66 68 69 70 73 74 75
76 77 78 79 80 81 82 85 86 87 88 92
95 96 97 99 100 101 102 103 104 105 106 108
109 110 111 113 114 115 116 117 1 18 120 121 122
123 124 125 126 127 128 129 130 131 132 133 134
135 136 137 138 141 142 143 144 145 146 147 148
149 151 153 154 155 156 157 158 160 161 162 164
165 166 167 168 169 170 171 172 174 176 177 178
179 180 181 183 184 185 186 187 188 189 190 191
196 199 201 202 203 205 206 207 208 209 210 213
214 217 218 219 222 223 224 236 244 245 247 249
263 264 267 268 271 273 274 278 280 282 283 284
285 286 287 288 289 290 291 292 293 294 298 299
300 301 302 303 304 305 306 307 308 309 310 312
313 315 318 320 322 323 324 325 326 327 328 329
331 333 336 337 338 339 341 342 343 345 346 347
348 349 350 351 352 353 354 356 357 358 359 360
361 363 364 365 366 371 374 375 379 380 382 384
386 387 388 389 390 391 393 394 395 396 397 398 400 401 404 413 415 416 418 419 420 421 422 426
427 435 440 449 452 453 466 467 468 469 470 471
473 474 484 486 489 490 497 502 503 504 507 508
510 512 513 514 517 519 521 523 524 525 526 527
528 532 533 535 544 545 552 555 556 557 573 582
584 587 589 590 592 593 594 599 604 608 621 623
300 ppm gave more than 70% control in these when compared to the untreated check which showed extensive disease development.
Example 6; Septoria Iycopersici (Leaf spot of tomato): Compounds were dissolved in 0.3% DMSO and then added to Potato Dextrose Agar medium just prior to dispensing it into Petri dishes. 5ml medium with compound in the desired concentration was dispensed into 60mm sterile petri-plates. After solidification each plate was seeded with 5mm size mycelial disc taken form periphery of actively growing virulent culture plate. Plates were incubated in growth chambers at 25°C temperature and 70% relative humidity for seven days and radial growth was
-ed. Compound s, 1 2 3 4 5 6 1 1 14 15 17
18 19 20 2j 24 25 26 27 28 29 30
31 33 35 36 37 40 41 44 45 46 47 48
49 51 52 65 66 68 69 70 73 74 75 76
77 79 80 81 82 85 86 87 88 91 92 95
97 99 100 101 102 103 104 105 106 107 108 109
110 111 113 114 115 116 118 120 121 122 123 124
125 126 127 128 129 130 131 132 133 134 135 136
137 138 141 142 144 145 146 147 148 149 151 153
155 157 158 160 161 164 165 166 167 168 169 170
172 174 176 177 178 179 180 181 183 184 185 188
190 195 196 199 201 202 203 205 206 207 208 209
210 213 214 218 219 222 223 224 235 236 244 245
247 249 263 264 267 268 278 280 281 282 283 284
285 286 288 289 290 298 300 301 302 304 305 306
307 308 310 312 313 315 320 3?? 323 324 325 326
327 328 329 331 333 336 337 338 339 341 342 343
345 346 347 370 371 374 375 379 380 382 383 386
388 389 390 391 393 394 395 396 397 398 400 401
402 404 415 416 419 421 427 435 437 440 447 453 466 467 468 469 470 471 472 473 474 484 486 488
489 490 497 498 502 503 504 507 508 509 510 511
512 513 517 519 523 524 525 526 57.7 528 533 545
552 557 573 585 592 593 599 608 624 633 at 300 ppm gave more than 70% control in these tests when compared to the untreated check which showed extensive disease development.
Example 7i Fusariuni cuimorum (Foot rot/Head blight of cereals): Compounds were dissolved in 0.3% DMSO and then added to Potato Dextrose Agar medium just prior to dispensing it into petri dishes. 5ml medium with compound in the desired concentration was dispensed into 60mm sterile petri-plates. After solidification each plate was seeded with a 5mm size mycelial disc taken from the periphery of actively growing virulent culture plates. Plates were incubated in growth chambers at 25 °C temperature and 60% relative humidity for seven days and radial growth was measured. Compounds 1 2 3 4 5 6 14 15
19 23 24 25 26 97 29 31 37 39 41 43
44 45 46 47 48 49 52 54 65 66 67 68
70 73 74 75 76 80 81 82 85 87 88 92
95 97 99 100 101 102 103 104 105 106 107 108
109 110 111 113 114 115 1 16 118 120 121 123 124
125 126 127 128 129 130 131 132 133 134 135 136
137 138 141 142 144 145 147 148 149 151 153 154
155 156 157 158 160 161 164 165 166 167 168 169
170 171 172 173 174 177 178 179 181 183 185 186
187 188 196 199 201 202 203 205 206 207 208 209
210 21 1 214 215 9 ] 7 218 219 222 993 224 236 244
247 263 no
Δ I 0 280 282 283 284 285 286 288 289 290
291 292 300 301 304 305 306 312 325 326 327 328
329 333 336 337 338 343 345 349 353 354 356 358
359 360 371 374 375 379 380 382 386 391 393 394
396 397 398 399 400 415 419 437 440 466 469 470
471 472 473 474 484 489 490 492 497 498 502 503
512 513 523 524 525 527 528 533 545 552 557 599
624 630 at 300 ppm gave 70% control in these ■■ tests when compared to the untreated check which showed extensive disease development. Example 8; Phytophthora infestans (Late blight of potato & tomato): Compounds were dissolved in 0.3% DMSO and then added to Rye Agar medium just prior to dispensing it into petri dishes. 5ml medium with compound in the desired concentration was dispensed into 60mm sterile petri-plates. After solidification each plate was seeded with a 5mm size mycelial disc taken from the periphery of actively growing virulent culture plates. Plates were incubated in growth chambers at 18°C temperature and 95% relative humidity for seven days and radial growth was measured. Compounds 5 6 49 52 70 74 76 101 103
109 114 115 116 121 123 126 127 129 130 132 145
174 177 179 224 244 278 280 282 283 284 285 286
288 289 290 291 292 300 301 304 305 306 325 326
327 328 329 333 337 338 343 345 349 353 354 356
358 359 360 371 374 375 379 380 382 391 393 394
396 397 398 399 400 419 437 440 466 469 470 471
472 473 474 484 489 490 497 498 502 503 512 513
523 524 525 527 528 533 545 552 557 599 624 630 at
300 ppm gave 70% control in these tests when compared to the untreated check which showed extensive disease development.
Example 9; Meloidogyne incognita (Root knot nematode):
Meloidogyne incognita : The test compounds at a concentration of 300 ppm were introduced into 500pL of distilled water containing 50 Meloidogyne incognita juveniles into 24-- well plates. The suspension was lightly shaken for uniform mixing of compounds. The test plates were covered with lids, and were kept for incubation at 25°C temperature and 90% RH. Dead/inactive nematodes were counted at an interval of 48, 72 and 96 hours under a microscope & the per cent mortality was calculated. Compounds 1 4 5 6 14 15
37 44 47 48 49 75 76 80 82 85 95 102
103 104 105 108 113 116 120 121 123 124 126 127
128 135 168 178 179 188 207 223 247 283 284 300
304 325 338 343 345 349 354 379 382 393 394 396
39 / at 300 ppm showed more than 90% mortality in the tests, where there was no mortality in the untreated check.
Having described the invention with reference to certain preferred aspects, other aspects will become apparent to one skilled in the art from consideration of the specification. It will be apparent to those skilled in the art that many modifications, both to materials and methods, may be practiced without departing from the scope of the invention.

Claims

WE CLAIM
Claim 1 : A compound of formula (I) or its agriculturally acceptable salts, metallic complexes, structural isomers, stereo-isomers, diastereoisomers, enantiomers, tautomers, or N-oxides thereof;
Figure imgf000143_0001
(I)
wherein,
1 ^ A
R represents hydrogen, halogen, cyano, nitro, N(R~)(R '), Cj -Ce-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, CrCe-haloaikyl, C2-C6-hal.oalkenyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, CrC6- haloalkoxy, sulfanyl, pentafluoro- 6-sulfanyl, pentafluoro- 6-sulfanyl-C1-C6-alkyl, Q-Ce- alkylsuifanyl, CrC6-halogenoalkyl.sulfanyl, CrC6-alkylsulfinyl, CrC6-halogenoalkylsulfinyl, Ci -C6-aikylsulfonyl, CrCe-halogenoalkylsulfonyl, Q-Ce-alkylsulfonyloxy, C5-C10- arylsulfonyloxy, C3-C6-carbocycle, C3-C6-heterocycle, each of these groups may be optionally substituted by halogen, cyano, CrC6-alkyl, CrCe-haloalkyl, carboxyl, CrCe-alkylcarbonyl, Cr C6-halogenoalkylcarbonyl;
R2 represents hydrogen, Cj -Ce-alkyl, Ca-Ce-alkenyl, Ca-Ce-alk nyl, Q-Ce-alkoxy or C3-C6- cycloalkyl which may be substituted by R7; or
R!and R2 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)m and Si(R")2, may form a five to eight membered ring, which for its part may be substituted by one or more of R ; Z is selected from the group consisting of CrC6-alkyl, C^-CValkenyl, C2-C6-alkynyl, wherein one or more carbon atoms may be replaced by heieroatoms selected from N, O and S or fused and/or nonfused C3-C12-carbocycle or fused and/or nonfused C3-C12-heterocycle, wherein one or more heteroatoms is selected from N, O and S, and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)m and Si(R")2, each of these groups may be optionally substituted by one or more groups of R8 or R8a or both;
T represents O, S, N(RS), N(OR5) or N-N(R5)(R6); 4
R and R may be same or differeni and is independently selected from hydrogen, d-Ce-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, d-d-alkylcarbonyl, d-Ce-alkenylcarbonyl, C2-C6- aikynylcarbonyl, Ci-Cg-alkylsulphonyl, Ci-Ce-alkylsulfonyloxy, Cj-Cio-arylsulfonyloxy, C=0(- NRxRy), wherein R and Ry may be same or different and is independently selected from hydrogen or d-Ce-alkyl; R3 and R4 may be optionally substituted by one or more groups of R ' ; or
R3 and R4 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)m and Si(R")2> may form a three to seven membered ring, which for its part may be substituted by one or more substituents independently selected from halogen, cyano, Ci-C6-alkyl, d-d-haloalkyl, carboxyl, Ci-C6- alkylcarbonyl, Ci-Ce-halogenoalkylcarbonyl; R5 and R6 may be same or different and is independently selected from hydrogen, Ci-Ce-alkyl, Ci-Ce- alogenoalkyl, d-Ce-alkoxy, d-Ce-halogenoalkoxy, d-Ce-alkoxy-Crd-alkyl, C2-Ce- alkenyl, C2-C6-halogenoalkenyl, C2-C6-alkynyl, d-Ce-halogenoalkynyl, C3-C6-cycloalkyl, C3- C6-cycloalkyl-d-C6-alkyl, C3-C6-halogenocycloalkyl, formyl, d-C6-alkylcarbonyl, d-C6- halogenoalkylcarbonyl, d-Ce-alkylsulphonyl, d-Ce-halogenoalkylsulphonyl, phenyl, naphthyl or phenylmethylene wherein R5 and Rb may be optionally substituted by one or more groups of R7;
R7 is selected from the group consisting of halogen, cyano, nitro, amino, d-C6-alkyl, d-C6- halogenoalkyl, Ci-Ce-alkoxy, Ci -Ce-halogenoalkoxy, Ci -Ce-alkylcarbonyl, d-C6- halogenoalkylcarbonyl, d-C6-alkoxycarbonyl, d-d-halogenoalkoxycarbonyl, d-C6- alkylaminocarbonyl, d-C6-di-alkylarrrinocarbonyl, carboxyl, CrC6-alkylsulfanyl, pentafluoro- 6-sulfanyl, non aromatic-C3-C6-carbocycle, non aromatic-Cs-Ce-heterocycle;
R8 is selected from the group consisting of hydrogen, halogen, nitro, cyano, -N(R3)(R4), hydroxyl, carboxyl, sulfanyl, amidine, -S(0)n(R9)=N-R10, -N=S(0)n(R9)(R10), pentafluoro-λ6- sulfanyl, pentafluoro A6-sulfanyl~Ci -C6-alkyl, d-C6-aIkyl, Ci-C6-halogenoalkyl, C2-C6-alkenyl,
C2-C6-halogenoalkenyl, C2-C6-alkynyl, C2-C6-halogenoalkynyl, Ci-Ce-alkoxy, d-C6- halogenoalkoxy, Ca-Ce-alkenyloxy, C2-C6-halogenoalkenyloxy, CrCe-alkynyloxy, C2-C6- halogenoalkynyloxy, Ci-Ce-alkoxy-Ci-Ce-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-d-C6-alkyl, C3-C6-halogenocycloalkyl, Ci-Ce-alkoxycarbonyl, Ci-Ce-alkylamino, d-Ce-alkoximino-d-Ce- alkyl, CrCe-alkylsulfanyl, Ci -CVhalogenoalkylsulfanyl, CrCe-alkylsulfinyl, CrC6- halogenoalkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-halogenoalkylsulfonyi, formyl, formyloxy, forniylamino, carbamoyl, N-hydroxycarbamoyl, carbamate, (hydroxyimino)-C1-C6-alkyl, Ci-Ce- alkylcarbonyl, C i -C6-halogenoalkylcarbonyl, C ·, -C6-alkylcarbamoyl, C i -C6-di-alkylcarbamoyl, CrCe-aikyloxycarbamoyl, CrCe-alkoxycarbamoyl, N-CrCe-alkyl-alkoxycarbamoyl-Ci-Ce- alkoxycarbonyl, Ci-Ce-halogenoalkoxycarbonyl, C j -C6-alkylaminocarbonyl, Ci-C6-di- alkylaniinocarbonyl, CrC6-alkylcarbonyloxy, CrCe-halogenoalkylcarbonyloxy, CrC6- alkylcarbonylamino, G. -C6-halogenoalkylcarbonylamino, Ci-Ce-alkylaminocarbonyloxy, C j -C6- di-alkylaminocarbonyloxy, Ci -Ce-alkyloxycarbonyloxy, d-Ce-alkoxyimino, Cj-Ce-iCj -Ce- alkoxyimino)-alkyl, C1-C6-(C2-C6-alkenyloxyimino)-alkyl, CrC6"(Ci -C16-aikynyloxyimino)- alkyl, (benzyloxyimino)-Cj -Ce-alkyl, Cj -C6~tri(alkyl)silyl, C¾ -C6-tri(alkyl)silyl-Ci~C6-alkyl, C3- C6-carbocycle, C3-C6-heterocycle, Cs-Cio-aryloxy, Cs-Qo-heteroaryloxy, Cs-Cio-arylsulfanyl, Cj-Cio-arylaiiiino, naphthyl, Cs-Cjo-arylmethylene and each of these groups may be optionally substituted by one or more groups of R ; or
R- and R' or two R together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)m and Si(R )2, may form a five to eight membered ring, which for its part may be substituted by one or more of R' ;
R8a represents pentafiuoro- °-sulfanyl or pentafluoro- 6-sulfanyl-Ci-C3 -alkyl;
R9 and Rk' may be the same or different represents hydrogen, cyano, CrCe-alkyl, CrC6- halogenoalkyl, C] -C6-alkoxy, CrCe-halogenoalkoxy, Cj-Ce-alkyicarbonyi, Ci -C6- alkoxycarbonyl, CrCe-halogenoalkoxycarbonyl, CrC6-alkylairtinocarbonyl, Q-Ce-di- alkylaminocarbonyl, d-Ce-alkylsulfanyl, C3-C6-carbocycle, C3-C6-heterocycle; or
R9 and R1 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)m and Si(R')2> may form a five to seven
7
membered ring, which for its part may be substituted by one or more of R ; n represents 0- 1 and m represents 1-2; and
provided that the following compounds are excluded from Formula ( I),
1) N-(4-(3,5-bis(trifluoromethyl)-lH-pyrazol-l-yl)phenyl)-4-methyl- l,2,3-tM
carbothioamide, 4-methyl-N-phenyl- 1 ,2,3-thiadiazoie-5-carbothioamide, N-(3-chloro-4- methylphenyl)-4-cyclopropyi- l,2,3-thiadiazole-5-cai¾othioamide, 4-cyclopropyl-N-(2,4- dimethoxyphenyl)-l,2,3-thiadiazole-5-carbothioamide, N-(4-(3,5-bis(trifluoromethyl)- lH-pyrazOl-l-yl)phenyl)-4-methyl-l,2,3-thiadiazole-5-carbothioamide;
2) T= N(R5), N(OR5), N-N(R5)(R6), R!= hydrogen or methyl and Z is not substituted with R' ~ in Formula 1 ;
3) T=0, R3= hydrogen, Cj -Ce-aikyi or cyclopropyl and Z is not substituted with RSa in Formula I;
4) the Formula A :
Figure imgf000146_0001
Formula A wherein
RIa from Ci-Ce-alkyl halides;
R a, RJa and R a selected from hydrogen, halogens, cyano, Nitro, Ci-Ce-halogenated alkyl, Ci-Ce-alkoxy, amino sulfonyl halides, Cj -Ce -sulfoxide base, Cj-C6 sulfone, CrC6- alkyl sulfonamide, phenyl, 1-5 same or different RSa substituted phenyl containing from 1 -3 same or different and selected from the oxygen atoms, nitrogen or sulfur atoms a 5-or-6-membered heterocyclic ring, 1-4 same or different R" " substituted containing from 1-3 same or different and selected from the oxygen atoms and nitrogen atoms or sulfur atoms of 5-or 6-membered ring, with the proviso that the R2a, Rja and R4a there can be only one hydrogen; R5a selected from halogens, nitro, nitrile, C Ce- alkyl, Ci-Ce -alkoxy, Ci-Ce-haiogenated alkyl or Ci-Gs- halogenated alkyl radicals.
Claim 2: Compound of formula (I) according to claim 1 wherein
Z is selected from the group consisting of Ci-Ce-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein one or more carbon atoms may be replaced by heteroatoms selected from N, O and S or fused and/or nonfused C3-C12-carbocycle or fused and/or nonfused C3-C12-heterocycle, wherein one or more heteroatoms is selected from N, O and S, and optionally including 1 to 3 ring members selected from the group consisting of C(=0), C(=S), S(0)m and Si(R2)2, each of these groups are substituted v^ith R ' and optionally substituted by one or more groups of RL : wherein R" represents pentailuoro- 6-sulfanyl or pentafluoro- 6-sulfanyl-CrC3-alkyl; and other definations are as defined in claim 1.
Claim 3: Compound of formula (I) according to claim 1 or 2 wherein Rl is selected from halogen, halogenoalkyl selected from -CHC12, -C(Rb)F2, -CHF2, -
C(Rb)2-CF3, -CHF-CF3, -CF2-CF3,-CHF-CF2-CF3, -CH2F, haloalkoxyalkyl selected from - C(Rb)2OCF3, -C(Rb)2OCHF2, -C(Rb)2OCH2F, -C1-C8-halogenoalkylsulfanyl-C1-C2-alkyl selcted from -C(Rb)2SCF3, -CH(Rb)SCF3, -C(Rb)2SCHF2, -CH(Rb)SCHF2j C C8-halogenoalkylsulfinyl- C C2-alkyl selected from -C(Rb)2SOCF3, -CH(Rb)SOCF3, -C(Rb)2SOC(Rb)F2, - CH(Rb)SOC(Rb)F2, Ci-Ce-alkyl-sulfonate-d-Ci-alkyl, Ci"C6-halogenoalkyl-sulfonate-Ci~C2- halogenoalkyl, pentaiIuoro- 6-sulfanyl-Ci-C3-alkyl, C3-C6-cycloalkyl-C 1 -C3-alky I , C3-C6- cycloalkyl-Ci"C3~halogenoalkyl, Cs-Ce-heterocyclyl-CrCs-alkyl, C3--C6-heterocyciyi--CV-C3-- halogenoalkyl; optionally each of these groups may be substituted by one or more groups of R ; wherein Rb represents, hydrogen, halogen, Ci-Ce-alkyl, Q-Ce-haloalkyl; and other definations are as defined in claim I,
Claim 4: A compound selected from a compound of formula (I) according to claim 1, 2 or 3 are: 4-(difiuoromethyl)-N-(3-(pentafluoro^ 4- (difluoromethyl)-N-(3-(pentafluoro-16-sulfaneyl)phenyl)- 1 ,2,3-thiadiazoie-5-carbothioamide; 4- (difluoroniethyl N-(4-(pentafluoro-16- 4- (difluoromethyl)-N-(4-(pentafluoro-i6-sulfaneyl)phenyl)-l,2,3-thiadiazole-5~c N- (2-chloro-4-(pentafluoro-16-sulfaneyl)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carboxamide; N-(2-chloro-4-(pentafluoro-16-sulfaneyl)phenyl)-4-(difluoromethyl)- 1,2,3 - thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-methyl-N-(3-(pentafluoro-16- sulfaneyl)phenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-methyl-N-(3- (pentafluoro-16-sulfaneyl)phenyl)-l,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N- methyl-N-(4-(pentafluoro-16-sulfaneyl)phenyl)-l,2,3-tliiadiazole-5-carboxarnide; 4- (difiuoiOmethyl)-N-methyl-N~(4-(pentafluoro-16-suifaneyl)phenyl)-l,2,3-thiadi
carbothioamide; N-(2-chloro-4-(pentai uoro-16-sulfaneyl)phenyl)-4-(difluoromethyl)-N-methyl- l,2,3-thiadiazole-5-carboxamide; N-(2,6-dichloro-4-(pentafluoro-16-sulfaneyl)phenyl)-4- (difluoromethyl)-l,2,3-thiadiazol.e-5-carboxaniide; N-(2,6-dibromo-4-(pentafl.uoro-16- sulfaneyl)phenyl)-4-(difluoromethyl)- 1 ,2,3 -thiadiazole-5-carboxamide; N-(2-bromo-4- (pentafluoro-16-sulfaneyl)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(2- biOmo-4-(pentafluoro-16-sulfaneyl)phenyl)-4-(difluoromethyl)- 1 ,2,3 -thiadiazole-5- carbothioamide; 4-(difluoromethyl)-N-(4-(methylthio)-3-(pentafluoro-16-sulfaneyl)phenyl)- 1 ,2,3 -thiadiazole-5-carboxamide; 4-(difluoiOmethyl)-N-(4-(metliylthio)-3 -(pentafluoro-16- sulfaneyl)phenyl)-l,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(4-fluoro-3- (pentafluoro-16-sulfaneyl)phenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(4- fluoro-3-(pentafluoro-16-sulfaneyl)phenyl)- 1 ,2,3-thiadiazole-5-carbothioamide; 4- (difluoromet yl)-N-(4-methoxy-3-(pentafluoro-16-sulfaneyl)phenyl)-l,2,3-thiadiazole-5- carboxamide; 4-(difluoromethyl)-N-(4-methoxy-3-(pentafluoro-16-sulfaneyl)phenyl)- 1,2,3- thiadiazole-5-carbothioamide; N-(3-(pentafluoro-16-sulfaneyl)phenyl)-4-(trifluoromethyl)- 1,2,3- thiadiaz.ole-5-carboxamide; N-(3-(pentafluoro-16-sulfaneyl)phenyl)-4-((rifluoromethyl)- 1,2,3- thiadiazole-5-carbothioaniide; N-(4-(pentaf uoro-16-sulfaneyl)phenyl 4-(trifl.uoromethyl)- 1,2,3- thiadiazole-5-carboxamide; N-(4-(pentafluoro-16-sulfaneyl)phenyl)-4-(trifluoromethyl)- 1,2,3 - thiadiazole-5-carbothioamide; N-(2-chloro-4-(pentafluoro-16-sulfaneyl)phenyl)-4- (trifluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(2-chloro-4-(pentafluoro-16- sulfaneyl)phenyl)-4-(trifluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; 4-methyl-N-(3- (pentafluoi -16-sulfaneyl)phenyl)- 1 ,2,3 -thiadiazole-5-carboxamide; 4-metiiyl-N-(3-(pentafluoro- 16-sulfaneyl)phenyl)- 1 ,2,3-thiadiazole-5-carbo(hioamide; 4-methyl-N-(4-(pentafluoro-16- sulfaneyl)phenyl)-l,2,3-thiadiazole-5-carboxaniide; N-(2-chloro-4-(pentafluoro-16- sulfaneyl)phenyl)-4-methyl- 1 ,2,3-thiadiazole-5-carboxamide; 4-isopropyl-N-(3-(pentafluoro-16- sulfaneyl)phenyl)-l ,2,3-thiadiazole-5-carboxamide; 4-isopropyI-N-(3-(pentafluoro-16- sulfaneyl)phenyl)- 1 ,2,3-thiadiazole-5-carbothioamide; 4-isopropyl-N-(4-(pentafluoro-16- sulfaneyl)plienyl)-l,2,3-thiadiazole-5-carboxaniide; 4-isopropyl-N-(4-(pentafluoro-!6- sulfaneyl)phenyl)-l,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(3- ((trifluoromethyl)thio)phenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3- ((trifluoromethyl)thio)phenyl)- l,2,3-tliiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(4- ((trifluoromethyl)thio)phenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(4- (( fluoromethyl)diio)phenyl)-l,2,3-thiadiazole-5-cai"bothioamide; N-(2-chloro-4- ((trifliioromediyl)thio)phenyl)-4-(difluoromethyl)-l,2,3-ihiadiazok N-(2-chloro- 4-((trifluoromethyl)thio)phenyl) -4-(difluoromethyl)- 1 ,2,3-thiadiazole- 5-carbothioamide; N-(4- cMoro-3-((trifluoromethyl)thio)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-ca^^ N- (2-bromo-5-((trifluoromethyl)thio)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-ca
N-(2-bromo-4-((trifluoromethyl)thio)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carboxamide; 4-(trifluoromethyl)-N-(4-((trifluoromethyl)thio)phenyl)-l ,2,3-thiadi^ carboxamide; 4-(trifluoromemyl)-N-(4-((trifluoromethyl)thio)phenyl)-l,2,3-thiadiazole-5- carbothioamide; 4-(difluoromemyl)-N-(4-((trifluoromethyl)sulfinyl)phenyl)-l,2,3-thiadiazole-5- carboxamide; N-(2-chloro-4-((trifluoiOmethyl)sulfinyl)phenyl)-4-(difluoromethyl)- 1 ,2,3- thiadiazole-5-carboxamide; N-(2-bromo-4-((trlfluoromethyl)sulfinyl)phenyl)-4-(dii uoromethyl)- l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3-((trifluoiOmethyl)sulfinyl)phenyl)- l,2,3-miadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3-((trifluoromethyl)sulfonyl)phenyl)- l,2,3-thiadiazole-5-carboxamide; N-(2-bromo-5-((trifluoromethyl)sulfonyl)phenyl)-4- (difluoromeiliyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3- (methylthio)phenyl)- l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3- (methylthio)phenyl)-l,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(4- (methylthio)phenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(4- (methylthio)phenyl)-l,2,3-thiadiazOle-5-carbot ioainide; 4-(difluoromethyl)-N-(2-fluoro-4- (methylthio)phenyl)-l.,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2-fluoro-4- (methylthio)phenyl)- l,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(2-fluoro-4- (methylthio)phenyl)-l,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(4- (methylsulfonyl)phenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(4- (me(hylsulfonyl)phenyl)-l ,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(3- (methylsulfinyl)phenyl)-l,2,3-thiadiazole-5-cai"boxamide; 4-(difluoromethyl)-N-(3- (methylsulfonyl)phenyl)- l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3- (methylsulfonyl)phenyl)-l,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(2- ( fluoromethoxy)phenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2- (trifluorornethoxy)phenyl)-l ,2,3-thiadiazole-5-carbothioai'nide; N-(4-bromo-2- ((rifluoromethoxy)phenyl)-4-(difluoromethyl)- 1 ,2,3-thiadiaz.ole-5-carboxamide; N-(4-bromo-2- ( fl.uoromethoxy)phenyl)-4-(difluoromethyl)-1.,2,3-thiadiazole-5-carbothioamide; 4- (difluoromethyl)-N-(3-((rifluoromethoxy)phenyl)-l,2,3-thiadiazole-5-carboxaniide; 4- (difluoromethyl)-N-(3-(trifluoromethoxy)phenyl)-l,2,3-t iadiazole-5-carbo(hioamide; 4- (difluoromethyl)-N-methyl-N-(3-(trifluorome^ 4- (difluoromeiJiyl)-N-meA^
N-(2-chloro-5-(trifluoromethoxy)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxaim N-(2-c oro-5-(trifluoromethoxy)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carbothioamide; N-(2,4-dichloro-5-(trifluoiOmethoxy)phenyl)-4-(difluoromethyl)- 1,2,3- thiadiazole-5-carboxamide; N-(2,4-dichloro-5-(trifluoromethoxy)phenyl)-4-(difluoromethyl)- l,2,3-thiadiazole-5-carbothioamide; N-(2-bromo-5-(trifluoromethoxy)phenyl)-4- (difluoromelhyl)-l,2,3-thiadiazole-5-carboxairiide; N-(2-bromo-5-(trifluoromethoxy)phenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; N-(2,4-dibromo-5- (trifluoromethoxy)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(2,4- dibronio-5-(triiiuofom 4- (difluoromethyl)-N-(4-(trifluoromethoxy)phenyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4- (difluoromethyl)-N-(4-(trifluoromethoxy)phenyl)-l,2,3-t iadiazole-5-carbo(hioamide; 4- (difluoromethyl)-N-methyl-N-(4-(trifluorom 4- (difluoromethyl)-N-methyl-N-(4-(trifluorom
N-(2-chlOro-4-(trifluoromethoxy)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carbothioamide; N-(2-bromo-4-(trifluoromethoxy)phenyl)-4-(difluoromethyl)- 1 ,2,3-thiadiazole- 5-carbothioamide; N-(2-biOmo-4-(trifluoiOmethoxy)phenyl)-4-(difluoromethyl)-N-methyl- 1,2,3- thiadiazole-5-carboxamide; N-(2-bromo-4-(trifluoromethoxy)phenyl)-4-(difluoromethyl)-N- methyl-l,2,3-thiadiazole-5-carbothioamide; N-(3-(difluoromethoxy)phenyl)-4-(difl.uoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(3-(difluoromethoxy)phenyl)-4-(difluoromethyl)- 1 ,2,3- thiadiazole-5-carbothioaniide; N-(3-(difl.uoromethoxy)phenyl)-4-(difluoromethyl)-N-methyl- l,2,3-thiadiazole-5-carboxamide; N-(3-(difluoromethoxy)phenyl)-4-(difluoromethyl)-N-methyl- l,2,3-thiadiazole-5-carbothioamide; N-(2,4-dichloro-5-(difluoromethoxy)phenyl)-4- (difluoromethyl)-l ,2,3-thiadiazole-5-carboxamide; N-(4-(difluoromethoxy)phenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(4-(difluoromethoxy)phenyl)-4- (difluoromethyl)- 1 ,2,3-thiadiazole-5-carbothioamide; N-(4-(difluoromethoxy)phenyl)-4- (difluoromethyl)-N-methyl-l,2,3-thiadiazole-5-carboxamide; N-(2-chloro-4- (difluoroniethoxy)phenyl)-4-(difluoromethyl)-l,2,3-thi diazole-5-carboxarnide; 4- (difluoromethyl)-N-(2-((rifluoromethyl)phenyl)-l,2,3-thiadiazole-5-carboxaini 4- (difluoromethyl)-N-(2-( fl.uoromethyl)phenyl)-l ,2,3-thiadiazole-5-carbothioaniide N-(4- chloro-2-(trifluoromethyl)phenyl)-4-(difl^ N-(4- bromo-2-(trifluoromethyl)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; N-(4- bronio-2-(trifluoromethy
carboxamide; 4-(difluoromethyl)-N-(4-fluoro-2-(trifluoromethyl)phenyl)-l,2,3-thiadiazole-5- carboxamide; 4-(difluoiOmethyl)-N-(4-fluoro-2-(tiifluoromethyl)plienyl)-l,2,3-tliiadiazole-5- carbothioamide; 4-(difluoromethyl)-N-(3-(trifluoromethyl)phenyl)-l,2,3-thiadiazole-5- carboxamide; 4-(difluoromethyl)-N-(3-(trifluoromethyl)phenyl)-l,2,3-thiadiazole-5- carbothioamide; 4-(difluoromethyl)-N-methyl-N-(3-(trifluoromethyl)phenyl)-l,2,3-thiadiaz.ole- 5-carboxamide; N-(2-chloro-3-(ti"ifluoromethyl)phenyl)-4-(difluoromethyl)-l,2,3-tliiadiazole-5- carboxamide; N-(2-chloro-3-(trifluoromelhyl)phenyl)-4-(difluoromethyl)-l,2,3-tMadiazole-5- carbothioamide; N-(4-chloro-3-(trifluoromethyl)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carboxamide; N-(4-chloro-3-( fluoromethyl)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carbothioami.de; 4-(difl.uoromethyl)-N-(4-( fluoromemyl.)phenyl.)-l ,2,3-thiadiazole-5- carboxamide; 4-(difluoromethyl)-N-(4-(trifluoromethyl)phenyl)-l,2,3-thiadiazole-5- carbothioamide; 4-(difluoromethyl)-N-methyl-N-(4-(trifluoromethyl)phenyl)-l ,2,3-thiadiazole- 5-carboxamide; N-(2-chloro-4-(trifluoromethyl)phenyl)-4-(difluorometliyl)-l,2,3-thiadiazole-5- carbothioamide; N-(2,6-dichloro-4-(trifluoromet yl)phenyl)-4-(difluoromethyl)- 1,2,3- thiadiazole-5-carbothioamide; N-(2-bromo-4-(trifluoromethyl)phenyl)-4-(difluoromethyl)- 1,2,3- thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(2-fluoro-4-(trifluoromethyl)phenyl)- 1,2,3- thiadiazole-5-carboxaniide; 4-(difluoromethyl)-N-(2-fluoro-4-(trifluorometb.yl)phenyl)- 1 ,2,3- miadiazole-5-carbothioarnide; N-(3,5-bis(trifluoromethyl)phenyl)-4-(difluoromethyl)- 1,2,3- thiadiazole-5-carboxamide; N-(3,5-bis(trifluoromethyl)phenyl)-4-(difluoromethyl)- 1,2,3- t iadiazole-5-carbothioamide; 4-(difluoroniethyl)-N-(2-methyl-4-(perfluoropropan-2-yl)phenyl)- l,2,3-ihiadiazole-5-carboxamide; N-(2-chlorophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carboxamide; N-(2-chlorophenyl)-4-(difluoromethyl)- 1 ,2,3-thiadiazole-5-carbothioamide; N- (2,4-dichlorophenyl)-4-(difluoromethyl)-l,2,3-thi diazole-5-carbothioamide; 4-(difluoromethyl)- N-(2,4,6-trichlorophenyl)- 1 ,2,3 -thiadiazole-5-carbothioamide; N-(2,3-dichlorophenyl)-4- (difluoroniethyl)-l ,2,3-thiadiazole-5-carboxamide; N-(2,3-dichlorophenyl)-4-(difl.uoromethyl)- 1 ,2,3-thiadiazole-5-carbothioamide; N-(2,5-dichlorophenyl)-4-(difluoromethyl)- 1 ,2,3- thiadiazole-5-carboxamide; N-(2-chloro-4-methylphenyl)-4-(difluoromethyl)-l,2,3-thiadiazole- 5-carboxamide; N-(3-chlorophenyl)-4-(difluoromethyl)- 1 ,2,3 -thiadiazole-5-carboxamide; -(3- cUorophenyl)-4-(difluorome(hyl)-l,2,3-t iadiazole-5-carbothioaniide; N-(3,4-dichlorophenyl)-4- (difluoromethyl)-l ,2,3-thiadiazole-5-carboxamide; N-(3,4-dichlorophenyl)-4-(difluoromethyl)- l,2,3-thiadiazole-5-carbothioamide; N-(3,5-dichlorophenyl)-4-(difluoromethyl)- 1,2,3- thiadiazole-5-carboxamide; N-(3-chloro-4-methylphenyl)-4-(difluoromethyl)-l,2,3-thiadiazole- 5-carboxamide; N-(3-chloro-4-methylphenyl)-4-(difluoromethyl)- 1 ,2,3-thiadiazole-5- carbothioamide; N-(4-chlorophenyl)-4-(difl.uoromethyl)-l,2,3-thiadiazole-5-carboxarnide; N-(4- cUorophenyl)-4-(difluoromemyl)-l,2,3-miadiazole-5-carbomioamide; N-(2-bromophenyl)-4- (difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(2-bromophenyl)-4-(difluoromet yl)- 1 ,2,3- thiadiazole-5-carbothioamide; N-(2-bromo-5-chlorophenyl)-4-(difluoromethyl)- 1,2,3- thiadiazole-5-carboxamide; N-(2-bromo-5-chlorophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carbothioamide; N-(2,4-dibromophenyl)-4-(difluoromemyl)-l ,2,3-thiadiazole-5-carbomioamide; N-(2-bromo-4-fluorophenyl)-4-(dii uoromethyl)-l,2,3-miadiazole-5-carboxainide; N-(2-bromo- 4-fluorophenyl)-4-(difluoromemyl)-l,2,3-miadiazole-5-carbomioamide; N-(2-bromo-3- memylphenyl)-4-(dii uoromethyl)-l,2,3-miadiazole-5-carboxainide; N-(3-bromophenyl)-4- (difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(3-bromophenyl)-4-(difluoromethyl)- 1 ,2,3- thiadiazOle-5-carbomioarnide; N-(4-bromophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carboxamide; 4-(difluoromethyl)-N-(2-fluorophenyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4- (difluorometliyl)-N-(2-fluorophenyl)- 1 ,2,3 -thiadiazole-5-carbothioamide; N-(4-chloro-2- fluorophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(4-chloro-2- fluorophenyl)-4-(difluoromemyl)-l,2,3-thiadiazole-5-cai"bodiioarnide; N-(3-chloro-2- fluorophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(3-chloro-2- fluorophenyl)-4-(difluoromethyl)- l,2,3-diiadiazole-5-carbomioarnide; N-(4-bromo-2- fluorophenyl)-4-(difluoromemyl)-l,2,3-miadiazole-5-carboxarnide; N-(4-bromo-2- fluorophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; N-(3-bromo-2- fluorophenyl)-4-(difluoromemyl)-l,2,3-thiadiazole-5-carboxamide; N-(3-bromo-2- fluorophenyl)-4-(difluoromethyl)-l,2,3-diiadiazole-5-carbothioamide; 4-(difluoromethyl)-N- (2,6-difluorophenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2,6- difluorophenyl)-l,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(2-fluoro-4- methylphenyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3-fluorophenyl)- 1 ,2,3- thiadiazole-5-carboxamide; 4-(difl.uoromethyl)-N-(3-fluorophenyl)- 1 ,2,3-thiadiazole-5- carbotiiioamide; 4-(difluoromethyl)-N-(3,4-diiluorophenyl)-l,2,3-tiiiadiazole-5-carboxamide; 4- (difluoroniethyl N-(3,4-difluorophenyl)-l ,2,3-thiadiazole-5-carbothioaniide; 4- (difluoromethyl)-N-(4-fluorophenyl)- l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(4- fluorophenyl)-l,2,3-thiadiazole-5-carbothioamide; N-(4-bromo-2-methylphenyl)-4- (difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(4-bromo-2-methylphenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carbothioaniide; 4-(diiluoromethyl)-N-(4-lluoro-2- methylphenyl)-l ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(4-fluoro-2- methylphenyl)- 1 ,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(p-tolyl)- 1 ,2,3- thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(p-tolyl)-l,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(perfluorophenyl)- 1 ,2,3-thiadiaz.ole-5-carboxamide; 4-(difluoromethyl)-N- (perfluorophenyl)-l ,2,3--thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(2,3,5,6- tetrafluorophenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2,3,5,6- tetrafluorophenyl)-l,2,3-t iadiazole-5-carbothioamide; N-(2-cyanophenyl)-4-(difluoromethyl)- 1 ,2,3 -thiadiazole-5-carboxamide; N-(4-chloro-2-methoxyphenyl)-4-(difluoromethyl)- 1 ,2,3 - thiadiazole-5-carboxarnide; N-(4-chloro-2-methoxyphenyl)-4-(difluoromet yl)-l,2,3-thiadiazole- 5-carbothioamide; 4-(difluoromediyl)-N-(3-methoxyphenyl)-l,2,3-thiadiazole-5-carboxamide; 4- (difluoromelhyl)-N-(3-methoxyphenyl)-l,2,3-thiadiazole-5-carbotMoainide; N-(2-chloro-3- methoxyphenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(4- methoxyphenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(4-methoxyphenyl)- 1 ,2,3-thiadiazole-5-carbothioamide; N-(2-chloro-4-methoxyphenyl)-4-(difluoromethyl)- 1 ,2,3- thiadiazole-5-carboxamide; N-(2-chloro-4-methoxyphenyl)-4-(difluoromethyl)- 1 ,2,3-thiadiazole- 5-carbothioamide; N-(2-chloro-4-(pentafluoro-16-sulfajieyl)phenyl)-4-methyl-l,2,3-thiadiazole- 5-carbothioamide; 4-methyl-N-(3-((trifluoiOmethyl)thio)phenyl)-l ,2,3-thiadiazole-5- carbothioamide; 4-methyl-N-(4-((trifluoromethyl)thio)phenyl)-l,2,3-thiadiazole-5- carbothioamide; 4-methyl-N-(3-(trifluoromethoxy)phenyl)- 1 ,2,3-thiadiazole-5-carbothioamide;
4-methyl-N-(4-(trifluoromethoxy)phenyl)-l,2,3-tWadiazole-5-carbot oamide; N-(2-chloro-4-
(trifluoromethoxy)phenyl)-4-metliyl- 1 ,2,3-thiadiazole-5-carbothioamide; N-(3 -
(difluoromethoxy)phenyl)-4-methyl-l,2,3-thiadiazole-5-carbotMoamide; N-(4-
(difluoroniethoxy)phenyl)-4-methyl-1.,2,3-thiadiazole-5-carbothioaniide; N-(3-fluorophenyl)-4- methyl- 1 ,2,3-thiadiaz.ole-5-carbothioamide; 4-methyl-N-(4-(methylthio)phenyl)- 1 ,2,3- thiadiazole-5-carbothioamide; 4-isopropyl-N-(3-((trifluoromethyl)thio)phenyl)- l,2,3-thiadiazole- 5-carbothioamide; 4-(difluoromethyl)-N-phenyl- 1 ,2,3-thiadiazole-5-carboxamide; 4- (difluoroniethyl)-N-phenyl-l,2,3-thiadiazole-5-carboxaniide; 4-(difluoromethyl)-N-(2- nitrophenyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3-nitrophenyl)- 1 ,2,3- thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(4-nitrophenyl)-l ,2,3-thiadiazole-5- carboxamide; 4-(difluoromethyl)-N-(4-nitrophenyl)- 1 ,2,3-thiadiazole-5-carbothioamide; N-(5- bromopyridin-2-yl)-4-(diiluoromethyl)-l ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N- (pyridin-3-yl)-l,2,3-thiadiazole-5-cai"bothioainide; N-(6-chloropyridin-3-yl)-4-(difluoromethyl)- l,2,3-thiadiazole-5-carbothioamide; N-(5,6-dichloropyridin-3-yl)-4-(difluoromethyl)- 1,2,3- thiadiazole-5-carbothioamide; N-(5-bromo-2-chloropyridin-3-yl)-4-(difluoromethyl)- 1,2,3 - thiadiazole-5-carbothioamide; N-(3-chloro-5-(trif uoromethyl)pyridin-2-yl)-4-(difluoromet yl)- l,2,3-thiadiazole-5-carbothioamide; 4-methyl-N-(3'-(pentafluoro-16-sulfaneyl)-[ l,r-biphenyl]-2- yl)-l,2,3-thiadiazole-5-carbothioamide; 4-isopropyl-N-(3'-(pentafluoro-16-sulfaneyl)-[l, - biphenylJ-2-yl)-l ,2,3-thiadiazole-5-carbothioamide; 4-isopropyl-N-methyl-N-(3'-(pentafl.uoro-16- sulfaneyl)-[l, -biphenyl]-2-yl)-l,2,3-t iadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(3'- (pentaf!uoro-16-sulfaneyl)-[ 1 , 1 -biphenyl]-2-yl)- 1 ,2,3-t adiazole-5-carbothioamide; 4- (difluoromethyl)-N-(3 '-(pentafluoro-16-sulf aneyl)- [ 1 , 1 '-biphenyl] -2-yl)- 1 ,2,3-thiadiazole-5- carbothioamide; (E)-N-(2-(N-cyano-S-isopropylsulfinin idoyl)phenyl)-4-methyl- 1 ,2,3- thiadiazole-5-carboxamide; N-(4'-(N-ethyl-S-methylsulfonirnidoyl)-[l, -biphenyl]-2-yl)-4- methyl- 1 ,2,3-thiadiazole-5-carboxamide; N-(4'-(N-(cyclopropylmethyl)-S-methylsulfonimidoyl)- [l, -biphenyl]-2-yl)-4-memyl- l,2,3-miadiazole-5-carboxamide; (E)-N-(3-(N-cyano-S- isopropylsulfinimidoyl)phenyl)-4-(difluoromemyl)-l,2,3-thiadiazole-5-carboxamide; N-(4-(N- cyanopropan-2-ylsulfonimidoyl)phenyl)-4-(difluoromemyl)-l,2,3-miadiazole-5-carboxamide; N- cyclohexyl-4-(difluoromethyl)-l,2,3-t adiazole-5-carboxamide; N-cyclohexyl-4- (difluoromethyl)- 1 ,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl )-N-isopropyl- 1 ,2,3- thiadiaz.ole-5-carboxamide; 4-(difluoromemyl)-N-isopropyl-l,2,3-miadiazole-5-carbothioamide; (4-(difluoromethyl)- 1 ,2,3-thiadiazol-5-yl)(moipliolino)niethanone; (4-(difluoromethyl)- 1 ,2,3- thiadiazol-5-yl)(morpholino)methanethione; (4-(difluoromethyl)- 1,2,3 -thiadiazol-5- yl)(thiomorpholino)methanone; (4-(difluoromethyl)-l,2,3-thiadiazol-5- yl)(thiomorpholino)methanethione; (4- (difluoromethyl)- 1 ,2,3-thiadiazol-5-yl)(4- methylpiperazin-l-yl)methanone; 4-(chloromethyl)-N-(4-(pentafluoro-16-sulfaneyl)phenyl)- l,2,3-thiadiazole-5-carboxamide; 4-(chloromethyl)-N-(3-(pentafluoro-16-sulfaneyl)phenyl)- l,2,3-thiadiazole-5-carboxamide; N-(3',4'-dichloro-5-fluoro-[l,r-biphenyl]-2-yl)-4- (difluoromethyl)-l ,2,3-thiadiazole-5-carboxamide; N-(3',4'-dichloro-5-fluoro-[ l,r-biphenyl]-2- yl)-4-(difluoromethyl)- 1 ,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(3',4',5'- trifluoro-[l,r-biphenyl]-2-yl)-l,2,3-ti[iiadiazole-5-carboxamide; 4-(dtfluoromethyl)-N-(3',4',5'- trifluoro-[l, -biphenyl]-2-yl)-l,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N- methoxy-N-( 1 -(2,4,6-trichlorophenyl)propan-2-yl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(3',4'- dichloro-5-fluoro-[l, -biphenyl]-2-yl)-4-isopropyl-l,2,3-thiadiazole-5-carboxamide; 4. isopropyl-N-(3^4^5'-trifluoro- l, -biphenyl]-2-yl)-l,2,3-thiadiazole-5-carboxaiTiide; N-(2-(3- chloro-5-(trifluoromethyl)pyridin-2-yl)ethyl)-4-isopropyl-l,2,3-tliiadiazole-5-carboxami^ N- (4'-chloro-[ l, -biphenylJ-2-yl)-4-methyl-l,2,3-thiadiazole-5-carboxainide; N-(3',4'-dichloro-5- fluoro [1,1 '-biphenyl] -2-yl)-4-methyl- 1 ,2,3-thiadiazole-5-carboxamide; 4-methyl-N-(3 ',4',5'- trifluoro-[l,r-biphenyl]-2-yl)-l,2,3-thiadiazole-5-carboxamide; N-(4'-chloro- [1,1 -biphenyl] -2- yl)-4-(difluoromethyl)- 1 ,2,3 -thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2-(4- methylpentan-2-yl)phenyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3- (isopropylthio)phenyl)- 1 ,2,3-thiadiazole-5-carboxaraide; 4-(difluoromethyl)-N-(3- (isopropylsuffinyl)phenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3- (isopropylsulfonyl)phenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2-(l - (isopropylthio)ethyl)phenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2-(l- (isopropylthio)ethyl)phenyl)-l,2,3-thiadiazole-5-carbothioamide; 4-methyl-N-(4-(pentafluoro-16- siilfaneyl)phenyl)-l,2,3-ihiadiazole-5-carbothioamide; N-(3-chloro-4-methylphenyl)-4-methyl- 1 ,2,3-thiadiazole-5-carbothioamide; 4-methyl-N-(m-tolyl)-l,2,3-lhiadiazole-5-carbothioamide; N-(3-isopropoxyphenyl)-4-methyl- 1 ,2,3-thiadiazole-5-cai¾otiiioamide; 4-methyl-N-phenyl- l,2,3-thiadiazole-5-carbothioamide; N-(2-chloro-4-(methylsulfonyl)phenyl)-4-(difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(2,6-dichlorophenyl)-4-(difluoromethyl)- 1 ,2,3 -thiadiazole- 5-carboxamide; N-(4'-chloro-[l, -biphenyl]-3-yl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carboxamide; N-([l ,l'-biphenyl]-3-yl)-4-(difluoromethyl)-l,2,3-tliiadiazole-5-carboxamide; N- (3',4'-difluoro-[ 1 , r-biphenyl]-3-yl)-4-(difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4- (difluoroniethyl)-N-(3',4',5'-trifluoro-[ 1 ,1.'-biphenyl]-3-yl )- 1 ,2,3-thiadiazole-5-carboxamide; 4- (difluoromethyl)-N-(3^4'-dimethyl-[l,r-biphenyl]-3-yl)-l,2,3-tMadiazole-5-carboxaim N-(4- (difluoromethoxy)phenyl)-4-(difluoromethyl N-methyl-l ,2,3-thiadiazole-5-carbothioaniide; 4- (difluorometliyl)-N-(2-((trifluoromethyl)thio)phenyl)-l,2,3-thiadiazole-5-carboxamide; 4- (difluoroniethy])-N-(2-((trifluoromeihyl)thio)phenyi)-l,^ N-(4- bromo-2-((trifluoromethyl)thio)phenyl)-4-(difluorom N- (2,4-dibromo-6-((trifluoromethyl)(hio)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carboxamide; N-(4-c oiO-2-((trifluoromethyl)thio)phenyl)-4-(difluoromethyl)- l,2,3-thiadiazole- 5-carboxamide; N-(2,4-dichloro-6-((trifluoromethyl)thio)phenyl)-4-(difluoromethyl)- 1,2,3- thiadiazole-5-carboxamide; N-(2-chloro-4-((trifluoromethyl)sulfonyl)phenyl)-4- (difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(4- ((trifluoromethyl)sulfonyl)phenyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3 - (((rifluoromethyl)sulfinyl)phenyl)-l,2,3-thiadiazole-5-carbothioainide; 4-(difluoromethyl)-N-(3- nitrophenyl)- 1 ,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(2-nitrophenyl)- 1 ,2,3- thiadiaz.ole-5-carbothioamide; N-(2-bromo-5-((trifluoromethyl)thio)phenyl)-4-(difluoromethyl)- l ,2,3-thiadiazole-5-carbothioaiTiide; N-(2-bromo-4-((trifluoromethyl)thio)phenyl)-4- (difluoromemyl)-l,2,3-miadiazole-5-carbomioamide; 4-(difluoromethyl)-N-(4- ((trifl.uoromethyl)sulfinyl)phenyl)-l ,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(3- (( fluoromethyl)sulfonyl)phenyl)-l,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(4- ((trifluoromethyl)sulfonyl)phenyl)-l ,2,3-(hiadiazole-5-carbothioamide; N-(2,6-dibromo-4- ((trifluoromethyl)thio)phenyl)-4-(difluoiOmethyl)- l,2,3-tliiadiazole-5-carboxamide; N-(3- (pentafluoro-16-sulfaneyl)phenyl)-4-(((trifluoromethyl)thio)methyl)-l,2,3-thiadiazole-5- carboxamide; N-(4-(pentafluoro-16-sulfaneyl)phenyl)-4-((( fluoromethyl)thio)rnethyl)- 1,2,3- thiadiaz.ole-5-carboxamide; 4-(difluoromet yl)-N-(4-(dimethylarnino)phenyl)-l,2,3-thiadiazole- 5-carboxamide; 4-(difluoromethyl)-N-(4-(dimethylamino)phenyl)-l ,2,3-thiadiazole-5- carbothioamide; N-(4-(tert-butyl)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(4-(tert-butyl)phenyl)-4-(difl.uoromethyl)-l,2,3-thi diazole-5-carbothioamide; N-(2-bromo-4- ((trifliioromediyl)siUfiiiyl)phenyl)-4-(difluoromeihyl)-l,2,3-thi N-(4- chloro-2-((trifluoromemyl)thio)phenyl)^
4-(difluoromemyl)-N-(2-((trifluorometh^ 4- (difluoronieiliyl)-N-(4-((difluoromeihyl)d«o)ph N~{4- bromo-2-((trifluoromethyl)sulfinyl)phenyl)-4-(difl^
4-(difluoromethyl)-N-(4-((difluoromethyl)^ N- (4-bromo-2-((trifluoiOmethyl)thio)phenyl)-4-(difluoromethyl)-l ,2,3-thiadiazole-5- carbothioamide; N-(2-chloro-4-(pentailuoro-16-sulfaneyl)phenyl)-4-(chloromethyl)- 1,2,3- thiadiazole-5-carboxamide; N-(4-bromophenyl)-4-(difluoromethyl)- 1 ,2,3-thi.adiazol.e-5- carbothioamide; 4-(difluoromethyl)-N-(2,4,6-tribromophenyl)-l,2,3-thiadiazole-5- carbothioami.de; N-(3,5-dichlorophenyl)-4-(difluoromemyl)-l,2,3-thiadiazol.e-5-carbothioamide; N-(2-cyanophenyl)-4-(difkioromethyl)-l,2,3-thiadiazole-5-cai-bothioamid N-(2,5- dichl.orophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; N-(2,6-dichlorophenyl)- 4-(difluoromethyl)- l,2,3-thiadiazole-5-carbothioamide; 4-(difluoromemyl)-N-(perbromophenyl)- l,2,3-thiadiazole-5-carboxamide; N-(2,6-dibromo-4-nitTophenyl)-4-(dif uoromethyl)- 1,2,3- thiadiazole-5-carboxamide; N-(3,5-dibromophenyl)-4-(difluoromethyl)-l,2,3-tliiadiazole-5- carboxamide; 4-(difluoromethyl)-N-(2,3,4-tribromophenyl)-l,2,3-thia.diazole-5-carboxamide; N-
(3,4-dibromophenyl)-4-(di.fluoromethyl)-l,2,3-thiadiazole-5-carboxaniide; N-(2,5- dibromophenyl)-4-(difluoromemyl)-l,2,3-thiadiazole-5-carboxamide; N-(3,4-dibromophenyl)-4- (difluorometliyl)-l,2,3-thiadiazole-5-carbotliioamide; N-(3,5-dibromophenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carbothioainide; N-(2,5-dibromophenyl)-4- (difluoromethyl)-l ,2,3-thiadiazole-5-carbothioamide; N-(2-bromo-6-fluoro-4-
( fluoromethyl)phenyl)-4-(difluoromethyl)-l,2,3-t adiazole-5-carboxamide; N-(3-chloro-5- ((triiluoromethyl)thio)pyridin-2-yl)-4-(diilu N-(4- chloro-2-(trifluoromethoxy)phenyl)-4-(difluorometo^ N-(4- chloro-2-(trifluoromethoxy)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboth 4- (difluoromethyl)-N-(2-methyl-4-(perfluoropropan-2-yl)phenyl)-l,2,3-thiadiazole-5- carbothioamide; (4-(difluoromethyl)-l,2,3-thiadiazol-5-yl)(4-phenyl-3,6-dihydropyridin-l(2¾ yl)methanone; N-(2,4-dibromo-6-(trifluoiOmethoxy)phenyl)-4-(difluoromethyl)- 1 ,2,3 - thiadiazole-5-carboxamide; N-(2,4-dibromo-6-(trifluoromethoxy)phenyl)-4-(difluoromethyl)- l,2,3-thiadiazole-5-carbothioamide; N-allyl-4-(difiuoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(prop-2-yn-l-yl)-l,2,3-thiadiazole-5-carboxainide; N-(2-bromo-6-methyl- 4-(perfluoropropan-2-yl)phenyl 4-(difluorom N-(2- chloro-4-(( fluoromethyl)sulfinyl)phenyl)-4-(difluoromethyl)-l,2,3-thiadiaz.ole-5- carbothioamide; N-(2-bromo-4-((trifluoromethyl)sulfonyl)phenyl)-4-(difluoromethyl)- 1,2,3- thiadiaz.ole-5-carbothioamide; N-(2,6-dibromo-4-((trifluoromethyl)thio)phenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; 4-(difluoromethyl)-N-(4- ((difluorometliyl)sulfonyl)phenyl)- l,2,3-thiadiazole-5-carboxainide; 4-(difluoromethyl)-N-(4- ((difluoromethyl)sulfonyl)phenyl)-l,2,3-thiadiazole-5-carbothioamide; 4-(chloromethyl)-N-(3- (trifkioromethoxy)phenyl)- l,2,3"thiadiazole-5-carboxamide; N-(2-chloro-4- ((difluoromethyl)thio)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamid 4- (difluorometliyl)-N-(4-((difluoromethyl)sulfinyl)phenyl)-l,2,3-thiadiazole-5-carboxamide; N- (2,4-dichloro-6-((rifluoromethoxy)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- 4-(diiluoroniethyl)-N-(4-((difluoromethyl)sulfinyl)pte
N-(2-c oro-4-(difluoromethoxy)phenyl)-4-(difl^^
N-(2,6-dibronio-4-(trifluoromethyl)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carbothioamide; N-(2-bromo-6-chloro-4-(trifluoromethyl)phenyl)-4-(difluoromethyl)- 1,2,3 - thiadiazole-5-carbothioamide; N-(2-bromo-6-fluoro-4-(trifluoromethyl)phenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; N-(3,5-dibromopyridin-2-yl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carboxa.mide; 4-(difluoromethyl)-N-(4-nitro-3- (trifluoromethyl)phenyl)- l,2,3-thiadiazole-5-carboxamide; N-(2-cyclopropyl-4- (trifluoromethyl)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; 4- (difluoroniethy])-N-(2-†]uoro-5-(tri†Iuoromethyl)phenyl)-l ,2 N-(5- cMoro-6-(methylthio)pyridin-3-yl)-4-(difluorom N-(2- bromo-4-(dffluoromethoxy)phenyl)^^ N-(2- bromo-4-(difluoromethoxy)phenyl)-4-(difluoro N- (2,4-dichlOro-5-(difluoromethoxy)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carbothioamide; N-(2,6-dibromo-4-((trifluoromethyl)sulfinyl)phenyl)-4-(difluoromethyl)- 1,2,3- thiadiazole-5-carboxamide; N-(2,6-dibromo-4-((trifluoromethyl)sulfonyl)phenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(2-bromo-6-chloro-4- (( iluoromethyl)thio)phenyI)-4-(difluorom N-(2,6- dichloro-4-((trifluoromethyl)thio)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole- N-(2-brorno-6-chloro-4-(((rifluoroniethyl)ihio)pheny1)- carbothioamide; N-(2,6-dichloro-4-((trifluoromethyl)thio)phenyl)-4-(difluoromethyl)- 1 ,2,3- thiadiazole-5-carbot ioamide; N-(benzo[d]isothiazol-5-yl)-4-(dif uoromet yl)-l,2,3-thiadiazole- 5-carboxamide; N-(5-chloro-6-(methylsulfonyl)pyridin-3-yl)-4-(difluoromethyl)-l,2,3- thiadiaz.ole-5-carboxamide; (4-(difluoromethyl)-l,2,3-thiadiazol-5-yl)(2,2,4-(rimethylquinolin- l(2H)-yl)methanone; N-(3-chlorophenyl)-4-(fluoromethyl)-N-rnethyl-l ,2,3-thiadiazole-5- carboxamide; 4-(difluoromethyl)-N-(2-fluoro-3-(trifluoromethyl)phenyl)- 1 ,2,3-thiadiazole-5- carboxamide; (4-(difluoromethyl)-l ,2,3-thiadiazol-5-yl)(3,4-dihydroquinolin-l(2H)- yl)methanone; N-(2,4-dichlorophenyl)-4-(dMuoromethyl)-N-methyl-l,2,3-thiadiazole-5- carboxamide; N-(4-chloro-3-fluorophenyl)-4-(difluoromethyl)-l ,2,3-diiadiazole-5-carboxamide; N-(3-c oiO-4-fluorophenyl)-4-(difluoromethyl)- l,2,3-thiadiazole-5-carboxaimde; N-(2,4- dibromophenyl)-4-(difluoromethyl)-N-methyl-l,2,3-thiadiazole-5-carboxamide; 5-(3- ((difluoiOmethyl)thio)phenyl)-4,5-di ydro-6H-pyiiOlo[3,4-d][l,2,3]thiadiazol-6-one; 4- (difluoromethyl)-N-methyl-N-(2,4,6- chlorophenyl)-l,2,3-t adiazole-5-carboxaniide; N-(4- chloro-3-fluorophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; N-(3-chloro-4- fluorophenyl)-4-(difluoromethyl)- 1 ,2,3 -thiadiazole-5-carbothioamide; N-(4-chloro-2- cyclopropylphenyl)-4-(difluoromethyl)-l.,2,3-thiadiazole-5-carboxamide; N-(2-bromo-4- (( fluoromethyl)su nyl)phenyl)-4-(difluorom N- (2,6-dichloro-4-(pentafluoro-16-sulfaneyl)phenyl)-4-(difl.uoromethyl)-l ,2,3-thiadiaz.ole-5- cai'bothioamide; N-(2-bromo-6-chloro-4-(pentafluoro-16-sulfaneyl)phenyl)-4-(difluoromethyl)- l,2,3-ihiadiazole-5-carboxamide; N-(2,6-dichloro-4-(pentafluoro-16-sulfaneyl)phenyl)-4- (difluoromethyl)-N-methyl- 1 ,2,3-thiadiazole-5-carboxamide; N-(2-cyclopropyl-4-(pentafluoro- 16-sulfaneyl)phenyl)-4-(difluoromethyl)-l,2,3-t adiazole-5-carboxamide; N-(2-bromo-6-chloro- 4-((trifluoromethyl)sulfinyl)phenyl)-4-(difluoro N- (2,6-dichloro-4-((triiluoromethyl)suliinyl)phenyl)-4-(difluoromethyl)-l,2,3-thiadia
carboxamide; N-(2,6-dibromo-4-((trifluoroniethyl)sulfinyl)phenyl)-4-(difluorornethyl)- 1,2,3- thiadiaz.ole-5-carbot ioamide; N-(2-bromo-6-chloro-4-(((jifluoromethyl)sulfinyl)phenyl)-4- (difluorometliyl)-l,2,3-thiadiazole-5-carbotliioamide; N-(2,6-dichloro-4-
Figure imgf000158_0001
cyclopropyl-N-(3,5-dichlorophenyl)-4-(difluoromethyl)-l,2,3-thi diazole-5-carboxamide; N-(2- bromo-4-((difluoromethyl)thio)phenyl)-4-(difl^ 4- (difluoromethyl)-N-(2-((difluoromethyl)^ 4- (difluoromethyl)-N-(2-((difluoromethyl)thio)^ ·(2·
Figure imgf000158_0002
1.2 J-ihiadia/ole -carb ihio mide: N-(4-chloro-2-((difluoromethyl)thio)phenyl)-4-(difluoiOmetliyl)-l,2,3-tliiadiazole-5- carboxamide; N-(4-bromo-2-((diiluoromethyl)thio)phenyl)-4-(dii uoromethyl)-l,2,3-thiadiazole- 5-carboxamide; N-(2-chloro-4-((difluorometliyl)sulfinyl)phenyl)-4-(difluoromethyl)- 1,2,3- thiadiazole-5-carboxamide; N-(4-chloro-2-((difluoromethyl)thio)phenyl)-4-(difluoromethyl)- l,2,3-thiadiazole-5-carbothioamide; N-(2-chloro-4-((difluoromethyl)sulfo yl)phenyl)-4- (difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2- ((difluoromethyl)sul inyl)phenyl)- 1 ,2,3-thiadiazole-5-carboxamide; (4-(difl.uoromethyl)- 1 ,2,3- thiadiazol-5-yl)(2,2,4-trimeth l-3 ,4-dihydroquinolin- 1 (2H)-yl)methanone; 4-(fluoromethyl)-N- (3-( fluoroniethyl)phenyl)-l,2,3-thiadiazole-5-carboxamide; N-cyclopropyl-4-(difluoromethyl)- N-(3-(trifluoromethoxy)phenyl)-l,2,3-thiadiazole-5-carboxaniide; N-cyclopropyl-4- (difluorome(hyl)-N-(4-(trifluoromeihoxy)phenyl) N- cyclopiOpyl-4-(difluoromethyl)-N-(3-(trifluoromethoxy)phenyl)-l,2,3-thiadiazole-5- carbothioamide; N-cyclopropyl-4-(difluoromethyl)-N-(4-(trifluoromethoxy)phenyl)- 1,2,3- thiadiazole-5-carbothioamide; N-cyclopropyl-4-(difluoromethyl)-N-(3-(pentafluoro-16- sulfaneyl)phenyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4-(fluoromethyl)-N-(4- (trifluoromethyl)phenyl)- l,2,3-thiadiazole-5-carboxamide; (4-(difluoromeihyl)-L2,3-thiadiazol- 5-yl)(8,8-dimethyldidlieno[3,2-b:2 3'-e]pyridin-4(8H)-yl)meihanone; N-(4'-chloro-[l,l'- biphenyl]-4-yl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxaniide; N-(2,6-dichloro-4- (( fluoromediyl)sulfonyl)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxaim N-(2- bromo-6-chloro-4-((trifluoromethyl)sulfo^
carboxamide; N-(2-cyclopropyl-4-((trifluoromethyl)thio)phenyl)-4-(difluoromethyl)- 1,2,3- thiadiazole-5-carboxaniide; 4-(chloromethyl)-N-(4-((trifluoromethyl)thio)phenyl)- 1,2,3- thiadiazole-5-carboxamide; 4-(chloromethyl)-N-(4-fluoro-3-(trifluoromethyl)phenyl)- 1,2,3- thiadiazole-5-carboxamide; 4-(chloromethyl)-N-(4-(trifluoromethoxy)phenyl)-l,2,3-thiadiazole- 5-carboxamide; 4-(difluoiOmethyl)-N-(2-((difluoromethyl)sulfinyl)phenyl)-l,2,3-tliiadiazole-5- carbothioamide; N-(2-chloro-4-((difluoromethyl)sulfonyl)phenyl)-4-(difluoromethyl)- 1,2,3- thiadiazole-5-carbothioamide; N-(3-(4-chlorophenoxy)phenyl)-4-(difluoromethyl)-l,2,3- thiadiaz.ole-5-carboxamide; 4-(difluoromethyl)-N-(3-phenoxyphenyl)- 1 ,2,3-thiadiazole-5- carboxamide; N-(3-(3,4-dichlorophenoxy)phenyl)-4-(difluoromethyl)-l,2,3-tliiadiazole-5- carboxamide; 4-(difluoromethyl)-N'-phenyl- 1 ,2,3-thiadiazole-5-carbohydraz.ide N'-(4- chlorophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carbohydrazide 4-(chloromethyl)-N-(3- (( fluoromethyl)thio)phenyl)-l,2,3-t adiazOle-5-carboxamide; 4-(thiocyanatomethyl)-N-(4- (trifluoromethoxy)phenyl)- 1 ,2,3-thiadiazole-5-carboxaraide; N-(4-fluoro-3- (trifluoromethyl)phenyl)-4-(thiocyanatomethyl)- l,2,3-thiadiazole-5-carboxainide; 4- (thiocyanatoniethy])-N-(3-((trifiuo^ 4- (thiocyanatomethyl -N-(4--((trffi (4- (difluoromethyl)-l,2,3-thiadiazol-5-yl)(3,4-dih^ 4- (difluorometliyl)-N-mediyl-N-(4-((trifluoromethyl)thio)phenyl)-l,2,3-thiadiazole-5- carboxamide; 4-(difluoromethyl)-N-methyl-N-(4-((tTifluoromethyl)sulfinyl)phenyl)- 1,2,3- thiadiazole-5-carboxamide; N'-(3,4-dichlorophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carbohydrazide 4-(difluoromethyl)-N-(3-((difluoromethyl)thio)phenyl)-l,2,3-thiadiazole-5- carboxamide; 4-(difluoromethyl)-N-(3-((trlfluoromethyl)thio)phenyl)-l ,2,3-thiadiazole-5- carboximidamide 4-(difluoromethyl)-N-(3-(trifluoromethyl)phenyl)-l,2,3-thiadiazole-5- carboximidamide 4-(difluoromethyl)-N-(3-(pentafluoro-16-sulfaneyl)phenyl)-l,2,3-thiadiazole-5- carboximidamide 4-(difluoromethyl)-N-(3-fluorophenyl)-l,2,3-thiadiazole-5-carboxiinidaini N-(3-bromophenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboximidamide N-([l,l'-biphenyl]- 4-yl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(4-cyanophenyl)-4- (difluoromethyl)-l ,2,3-thiadiazole-5-carboxamide; N-(4-bromo-2-(trifluoromethyl)phenyl)-4- (moipholinomethyl)-l ,2,3-thiadiazole-5-carboxamide; 4-(morpholinomethyl)-N-(3-(pentafluoro- 16-sulfaneyl)phenyl)- 1 ,2,3-thiadiazole-5-carboxamide; ethyl 4-(4-(difluoromethyl)- 1 ,2,3- thiadiazole-5-carboxamido)benzoate ethyl 3-(4-(difluoromethyl)-l,2,3-thiadiazole-5- carboxamido)benzoate N-(3-(pentafluoro-16-sulfaneyl)phenyl)-4-(thiocyanatomethyl)- 1,2,3- thiadiazole-5-carboxaniide; 4-(thiocyanatomethyl)-N-(3-(tri.fluoromethoxy)phenyl)- 1,2,3- thiadiaz.ole-5-carboxamide; N-(4-(difluoromethoxy)phenyl)-4-(thiocyanatomethyl)- 1,2,3- thiadiazole-5-carboxamide; N-(3-(difluoromethoxy)phenyl)-4-(thiocyanatomethyl)- 1,2,3- diiadiazole-5-carboxamide; 4-(tiiiocyanatomethyl)-N-(3-(trifluorometiiyl)phenyl)-l,2,3- thiadiazole-5-carboxaniide; 4-(chloromethyl)-N-(3-(difluoromethoxy)phenyl)-l ,2,3-thiadiazole- 5-carboxamide; 4-(chloromethyl)-N-(4-(difluoromethoxy)phenyl)-l,2,3-thiadiazole-5- carboxamide; 4-((4-methylpiperazin- 1 -yl)methyl)-N-(3-(trifluoromethyl)phenyl)- 1 ,2,3- thiadiazole-5-carboxamide; 4-((4-metliylpiperazin-l-yl)methyl)-N-(3-(trifluoromethoxy)phenyl)- l,2,3-thiadiazole-5-carboxamide; 4-((4-methylpiperazin-l-yl)methyl)-N-(4- (trifl.uoromethoxy)phenyl)-l,2,3-thiadiazole-5-carboxai'nide; 4-((4-methylpiperazin-l- yl)methyl)-N-(4-((trifluoromethyl)thio)phenyl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(4-fluoro-3- (trifluoromethyl)phenyl)-4-((4-methylpiperazin-l-yl)methyl)- l,2,3-t adiazole-5-carboxam N-(4-chlorophenyl)-4-((4-methylpiperazin-l-y^ 4-((4- methylpiperazin- 1 -yl)methyl)-N-(3-(pentafl.uoro-16-sulfaneyl)phenyl)- 1 ,2,3-thiadiazole-5- carboxamide; N-(3\4,-difluoro-[l, -biphenyl]-2-yl)-4-(difluoromethyl)-l,2,3-thiadiazole-5- carboxamide; 4-(difluoromethyl)-N-(thiazol-2-yl)- 1 ,2,3-thiadiazole-5-carboxamide; 4- (difluoromet yl)-N-(lH-pyrazol-3-yl)-l,2,3-thiadiazole-5-carboxamide; N-(benzo[d]thiazol-2- yl)-4-(difluoromethyl)-1.,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(pyridazin-4-yl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(3-(trifluoromethoxy)phenyl)-4-(trifluoromethyl)- 1 ,2,3- thiadiazole-5-carbothioamide; N-(2-chloro-4-((trifluoromet yl)thio)phenyl)-4-(trifluoromethyl)- 1 ,2,3 -thiadiazole-5-carbothioamide; N-(2-chloro-4-(trifluoromethoxy)phenyl)-4- (trifluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; N-(4-(lrifluoromethoxy)phenyl)-4- (trifl.uoromethyl)- 1 ,2,3-thiadiazole-5-carbothioamide; 4-(trifluoromethyl )-N-(3-
(( fluoromethyl)thio)phenyl)-l,2,3-thiadiazole-5-carbot ioainide; N-(2-cyclopropyl-4- (trifluoromethoxy)phenyl)-4-(trifluoromethyl)-l,2,3-thiadiazole-5-carbothioam N-(4- cMorophenyl)-4-(trifluoromethyl)-l,2,3-lhiadiazole-5-carbothioamide; 4-(trifluoromethyl)-N-(3- ( fluoromethy pheny -l ^^-thiadiazole-S-carbothioaiTiide; N-(3-chlorophenyl)-4- (trifliioromethyl)-l,2,3-ihiadiazole-5-cailiodiioamide; 4-(fluoroniethyl)-N-(4-methoxybenzyl)-N- methyl-l,2,3-thiadiazole-5-carboxamide; N-(3',4'-difluoro-[l,r-biphenyl]-2-yl)-4-methyl- 1,2,3- thiadiazole-5-carbothioamide; 4-(difluorometliyl)-N-(5-(trifluoromethyl)-l,3,4-thiadiazol-2-yl)- l,2,3-t iadiazole-5-carboxamide; 4-(morpholinomet yl)-N-(4-(trifluoromethyl)phenyl)- 1,2,3- thiadiazole-5-carboxamide; N-(3-chlorophenyl)-4-(thiomorpholiiiometiiyl)-l,2,3-thiadiazole-5- carboxamide; 4-(thiomorpholinomethyl)-N-(3-((trifl^
5-carboxamide; 4-(thiomorpholinomethyl)-N-(3-( fluoromethyl)phenyl)-l,2,3-thiadiazole-5- carboxamide; N-(2-chloro-4-(trifluoromethyl)phenyl)-4-(thiomorpholinomethyl)- 1,2,3- thiadiazole-5-carboxamide; 4-(diiluoromethyl)-N-(2-((3E,5E,6E)-5-(methoxyimino)-4,6- dimet yl-2,8-dioxa-3,7-diazanona-3,6-dien-l-yl)phen^ N- (2,2-dif luorobenzo[d] [ 1 ,3]dioxol-5-yl)-4-(difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4- (difluorometliyl)-N-hydroxy-l,2,3-tliiadiazole-5-carboximidamide N-(4-chlorophenyl)-4- (fluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(2-chloro-4-(tri.fluoromethyl)phenyl)-4- (fluoromethyl)- l,2,3-tliiadiazole-5-carboxamide; 4-(fluoromethyl)-N-(3-(pentafluoro-16- sulfaneyl)phenyl)-l,2,3-thiadiazole-5-carboxamide; N-(3-chlorophenyl)-4- (((trifluoromethyl)thio)metliyl)-l,2,3-thiadiazole-5-cai"boxaniide; N-(3-(trifluoromethyl)phenyl)- 4-(((tTifluoromethyl)thio)methyl)-l,2,3-thiadiazole-5-carboxamide; N-(4-chlorophenyl)-4- (((triiluoromethyl)thio)niethyl)-l,2,3-thiadiazole-5-carboxamide; 4- (((trifluoromethyl)thio)methyl)-N-(4-((^ carboxarnide; 4-(((trifluoromethyl)thio)methyl)-N-(3-((trifluoromethyl)tliio)phenyl)- 1,2,3- thiadiazole-5-carboxamide; N-(4-(trifluoromet oxy)phenyl)-4-(((trifluoromethyl)thio)methyl)- l,2,3-thiadiazole-5-carboxamide; N-(3-(trifluoromethoxy)phenyl)-4- (((trifluoromethyl)thio)methyl)-l,2,3-thiadiazole-5-carboxainide; N-(2,4-dichlorophenyl)-4- (fluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(2-fluoro-3-(trifluoromethyl)phenyl)-4- (fluoromethyl)-l,2,3-thiadiazole-5-cai"boxamide; 4-(fluoromethyl)-N-(2- (trifl.uoromethyl)phenyl)-l ,2,3-thiadiazole-5-carboxaniide; N-(4-(trifluoromethyl)phenyl)-4- (((trifluoromethyl)tliio)metliyl)- l,2,3-tliiadiazole-5 -carboxarnide; N-(2-chloro-4- (irifluoromeihyl)phenyl)-4-((((rifluoromeii^ 4- (fluoromethyl)-N-(3-( fluoromethoxy)phenyl)-l,2,3-thiadiazole-5-cai"boxarnide; 4- (fluoromethyl)-N-(4-(trifluorome(hoxy)phenyl)-l,2,3-thiadiazole-5-carboxamide; N-(4-chloro-2- fluorophenyl)-4-(fluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(4-chlorophenyl)-4- (((trifluoromethyl)sulfinyl)methyl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(3- (triiluoroniethyi)phenyi)-4-(((tiifluoromethyl)
N-(3-cyclopropyl-5-methylphenyl)-4-(difluorom N-(3- cyclopropylphenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(3,5- dimethylphenyl)-4-(fluoromethyl)- 1 ,2,3-thiadiaz.ole-5-carboxamide; N-(3- (cyclopropylethynyl)phenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; 4- (difluorometliyl)-N-(o-tolyl)-l,2,3-tliiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(m-tolyl)- 1 ,2,3-t iadiazole-5-carboxamide; 4-(difluoromethyl)-N-(5-fluoro-2-methylphenyl)- 1 ,2,3- thiadiazole-5-carboxamide; N-(5-chloro-2-methylphenyl)-4-(difluoromethyl)- 1,2,3 -thiadiazole- 5-carboxamide; 4-(difluoromethyl)-N-(2-iodo-5-methylphenyl)- 1 ,2,3-thiadiazole-5- carboxamide; 4-(difluoromethyl)-N-(2-methyl-5-( fluoromethyl)phenyl)-l,2,3-thiadiazole-5- carboxamide; 4-(difluoromethyl)-N-(4-methyl-3-( fluoromethyl)phenyl)-l,2,3-thiadiazole-5- carboxarnide; 4-(difluoromethyl)-N-(4-fluoro-3-me^
4- (difluoromethyl)-N-(3-fluoro-4-methylphenyl)-l,2,3-thiadiazole-5-carboxainide; N-(4-bromo- 2,5-diniethylphenyl)-4-(difluoromethyl)-l ,2,3-thiadiazole-5-carboxamide; N-(4-bromo-2-fl.uoro-
5- metliylphenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(4-bromo-2-chloro-5- methylphenyl)-4-(difl.uoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(3-fluoro-5- methylphenyl)-4-(trifluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; N-(3,5-dichlorophenyl)- 4-(trifluorome(hyl)-l,2,3-thiadiazole-5-carbothioamide; N-(3-chloro-5-methylphenyl)-4- (trifluoromethyl)- l,2,3-thiadiazole-5-carbothioamide; N-(3-bromo-5-methylphenyl)-4- (dilluoromethyl)-l ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3-fluoro-5- methylphenyl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(3-chloro-5-methylphenyl)-4- (difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxarnide; N-(4-(trifluoromethoxy)phenyl)-4- (((trifluoromethyl)sulfinyl)melhyl)-l ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3,5- dimethylphenyl)-l,2,3-thiadiazole-5-carboxainide; N-(3-(trifluoromethoxy)phenyl)-4- (((triiluoromethyl)sulfinyl)methyl)-l,2,3-thiadiazole-5-carboxaniide; N-(3,5- dicyclopropylphenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)- N-(3-fluoro-5-methylphenyl)-l,2,3-thiadiazole-5-carbothioamide; N-(3-bromo-5-methylphenyl)- 4-(difluoromethyl)-l,2,3-thiadiazole-5-cai-bothioamide; 4-(difluoromethyl)-N-(3,5- dimethylphenyl)-l,2,3-thiadiazole-5-carbothioamide; N-(3-chloro-5-methylphenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; N-(3-chloro-5-metliylphenyl)-4- (difluoromethyl)-N-methyl-l,2,3-thiadiazole-5-carboxamide; N-(3-bromo-5-methylphenyl)-4- (difluorometliyl)-N-methyl-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3,5- dimethylphenyl)-N-methyl-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3-lluoro-5- methylphenyl)-N-methyl-l ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2,5- dimethylphenyl)- 1 ,2,3 -thiadiazole-5-carboxamide; N-(2-bromo-5-methylphenyl)-4- (difluorometiiyl)-l,2,3-thiadiazole-5-carboxamide; N-(3-aminophenyl)-4-(difluoromethyl)- 1 ,2,3- thiadiazole-5-carboxamide; N-(3-cyclopropylphenyl)-4-(fluoromethyl)- 1 ,2,3-thiadiazole-5- carboxamide; N-(3-bromophenyl)-4-(fluoromethyl)-l,2,3-thiadiazole-5-carboxaniide; 4- (fluoromethyl)-N-(4-methoxybenzyl)-l,2,3-thiadiaz.ole-5-carboxamide; N-(2-chloro-5- methylphenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2- fluoro-5-methylphenyl)-l ,2,3-thiadiazole-5-carboxarnide; 4-(difluoromethyl)-N-(5,6,7,8- tetrahydronaphthalen- 1-yl)- 1 ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-( 1 ,2,3,4- tetraliydronaphthalen-l-yl)-l,2,3-thiadiazole-5-cai"boxaniide; N-(2-bromo-4-metliylphenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(2-chloro-5-methoxyphenyl)-4- (difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(3 -chloro-2-methylphenyl)-4-
(difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2,3-dihydro-lH-inden- 4-yl)- 1 ,2,3-thiadiazole-5-carboxaniide; N-(4-chloro-3-(difluoromethyl)phenyl)-4- (chloromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(4-chloro-3-(difluoromelliyl)phenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carbothioamide; N-(4-chloro-3-(difluoromethyl)phenyl)-4- (difluoromethyl)-l,2,3-thiadiazole-5-carboxamide; N-(4-chloro-3-(difluoromethyl)phenyl)-4- (difluoroniethyl)-N-niethyl-l ,2,3-thiadiazole-5-carboxamide; N-(3-cyclopropyl-5- methylphenyl)-4-(difluoromethyl)-l,2,3-thiadiazole-5-carbothioainide; N-(4-chloro-3- (difluoromethyl)phenyl)-4-(((trifluorome(hyl)thio)methyl)-l,2,3-thiadiazole-5-c 4- (difluoromethyl)-N-mediyl-N-(5,6,7,8-tetrahydronaphthalen- 1-yl)- 1,2,3 -thiadiazole-5- carboxamide; 4-(difluoromethyl)-N-(5-fluoro-2-methylphenyl)-N-methyl-l,2,3-thiadiazole-5- carboxamide; N-(5-chloro-2-methylphenyl)-4-(difluoromethyl)-N-methyl-l,2,3-thiadiazole-5- carboxamide; 4-(difluoromethyl)-N-(2,5-dimethylphenyl)-N-metliyl-l,2,3-thiadiazole-5- carboxamide; 4-(difluoromethyl)-N-methyl-N-(o-tolyl)- 1 ,2,3-thiadiazole-5-cai¾oxamide; 4- (difluoromethyl)-N-methyl-N-(2-methy^
carboxamide; 4-(difluoromethyl)-N-(2-fluoro-5-methylphenyl)-N-methyl-l,2,3-thiadiazole-5- carboxamide; N-(3-chloro-2-methylphenyl)-4-(difluoromethyl)-N-methyl-l,2,3-thiadiazole-5- carboxamide; N-(2-bromo-4-methylphenyl)-4-(difluorom
carboxamide; 4-(difluoromethyl)-N-(2-methoxyphenyl)- l,2,3-thiadiazole-5-carboxai'nide; 4- (difiuoromethyl)-N-(2-methoxy-5^ N-(4- biOmonap ialen-l-yl)-4-(difluoromethyl)- l,2,3-thiadiazole-5-carboxainide; 4-(difluoromethyl)- N-(3-isopropoxyphenyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(6- methylpyiidin-2-yl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3-fluoro-4- methylphenyl)-N-methyl- 1 ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-methyl-N-(4- methyl-3-(trifluoromethyl)phenyl)-l,2,3-thiadiazole-5-carboxaiTiide; 4-(difluoromethyl)-N-(4- fluoro-3-methylphenyl)-N-methyl-l,2,3-thiadiazole-5-carboxainide; 4-(difluoromethyl)-N-(3- isopropoxyphenyl)-N-methyl-l.,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2- methoxy-5-methylphenyl)-N-methyl-l,2,3-thiadiazole-5-carboxarnide; N-(4-bromonaphthalen-l- yl)-4-(difluoromethyl)-N-methyl-1.,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(2- methoxyphenyl)-N-methyl-l,2,3-thiadiazole-5-carboxainide; N-(4-bromo-2,5-dimethylphenyl)- 4-(difluoromethyl)-N-methyl-l,2,3-thiadiazole-5-carboxarnide; N-(4-chloro-3- (fluoromediyl)phenyl)-4-(difluoromediyl)-l,2,3-thiadiazole-5-carboxamide; N-(2-bromo-4- chloro-5-(difluorornemyl)pte N-(2- bromo-4-chloro-5-(difluoromethyl)phenyi)-4-^^
4-(difluoromethyl)-N-(2,6-dimethylphenyl)-l,2,3-tMadiazole-5-carboxamide; N-(4-bromo-3- methylphenyl)-4-(difluoromethyl)- l,2,3-thiadiazole-5-carboxamide; 4-(chloromethyl)-N-(3,5- dimethylphenyl)-l,2,3-thiadiazole-5-carboxarnide; 4-(chloromethyl)-N-(3-fluoro-5- methyl phenyl)- 1 ,2,3-thiadiazole-5-carboxaniide; N-(3-chloro-5-methylphenyl)-4- (chloromethyl)-l,2,3-thiadiazole-5-cailioxamide; 4-(chloromethyl)-N-(3,5-dichlorophenyl)- l ,2,3-thiadiazole-5-carboxamide; 4-(chloromethyl)-N-(3,5-difluorophenyl)-l ,2,3-thiadiazole-5- carboxamide; N-(3 -chloro-5-methylphenyl)-4-methyl- 1 ,2,3-t adiazole-5-carbothioamide; N-(3- fluoro-5-methylphenyl)-4-methyl-l ,2,3-thiadiazole-5-carbothioaniide; 4-(difluoromethyl)-N-(2- ethylphenyl)-l ,2,3-thiadiazole-5-carboxamide; 7-bromo-5-(3-(trifluoromethyl)phenyl)- [l ,2,3]thiadiazolo[5,4-c]pyridin-4(5H)-one; 4-(difluoromethyl)-N-(2-fluoro-5- (trifluoromethyl)phenyl)-N-methyl-l,2,3-thiadiazole-5-carboxamide; 4-(chloromethyl)-N-(2- ethylphenyl)-l ,2,3-thiadiazole-5-carboxamide; N-(2-bromo-4-chloro-3-(dif uoromethyl)phenyl)- 4-(difluoromethyl)-l.,2,3-thiadiazole-5-carboxamide; N,N-dicyclohexyl-4-(difl.uoromethyl)- l,2,3-thiadiazole-5-carboxamide; N-(3,5-dichlorophenyl)-4-(((trifluoromethyl)thio)methyl)- 1 ,2,3 -thiadiazole-5-carboxamide; N-(3-chloro-5-methylphenyl)-4- (((trifluoromethyl)thio)methyl)-l,2,3-thiadiazole-5-carboxamide; N-(3-bromo-5-methylphenyl)- 4-((( fluoroniethyl)thio)methyl)-1.,2,3-thiadiazole-5-carboxamide; N-(3-fluoro-5- methylphenyl)-4-(((trifluoromethyl)thio)methyl)-l,2,3-thiadiazole-5-c N-(3,5- diniethylphenyl)-4-(((trifluoromethyl)tliio)nieth 4- (difluorometliyl)-N-(2-fluorobenzyl)-N-metliyl-l,2,3-thiadiazole-5-carboxamide; 4- (difluoroniethyl N-(5-methylpyndin-2-yl)-l,2,3-thiadiazole-5-carboxarnide; N-(4-chloro-3- (difluoromethyl)phenyl)-4-(fluoiOmethyl)-l,2,3-tliiadiazole-5-carboxamide; 4-(difluoromethyl)- N-(2,6-dimethylphenyl)-N-methyl- 1 ,2,3-thiadiazole-5-carboxamide; N-(4-bromo-3- methylphenyl)-4-(difluoromethyl)-N-methyl- l,2,3-thiadiazole-5-carboxainide; 4-(chloromethyl)- N-(3,5-dichlorophenyl)-N-methyl-l ,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(4- ethylthiazol-2-yl)-l ,2,3-thiadiazole-5-carboxamide; N-(4'-chloro-5-methyl-[ l,1.'-biphenyl]-3-yl)- 4-(difluoromethyl)- 1 ,2,3-thiadiazole-5-carboxamide; N-(3 ',4'-dichloro-5-methyl- [1,1 '-biphenvl] - 3-yl)-4-(difluoromethyl)-l ,2,3-thiadiazole-5-carboxamide; 5-(4-chlorophenyl)-4,5-dihydro-6H- pyrrolo[3,4-d][l,2,3]thiadiazol-6-one; 5-(4-(trifluoromethoxy)phenyl)-4,5-dihydro-6H- pyrrolo[3,4-d][l ,2,3]thiadiazol-6-one; 5-(3-(trifluoromethoxy)phenyl)-4,5-dihydro-6H- pyrrolo[3,4-d][l,2,3]thiadiazol-6-one; 5-(3-((trMuoromet yl)thio)phenyl)-4,5-dihydro-6H- pyrrolo[3,4-d][l,2,3]thiadiazol-6-one; 5-(4-((trifluoromethyl)thio)phenyl)-4,5-dihydro-6H- pyrrolo[3,4-d][l,2,3]thiadiazol-6-one; 5-(3-chlorophenyl)-4,5-di ydro-6H-pynOlo[3,4- d][ l,2,3]thiadiazol-6-one; 5-(3-(trifluoromethyl)phenyl)-4,5-dihydro-6H-pyrrolo[3,4- d][ l,2,3]thiadiazol-6-one; 5-(4-((difluoromethyl)thio)phenyl)-4,5-dihydiO-6H-pyrrolo[3,4- d][l,2,3]thiadiazol-6-one; 5-(3,5-dichlorophenyl)-4,5-dihydro-6H-pyrrolo[3,4- d][l,2,3]tliiadiazol-6-one; 5-(3-(trifluoromethoxy)phenyl)-6,7-dihydro-[l,2,3]tliiadiazolo[5,4- c]pyridin-4(5H)-one; 5-(3-( fluoromethyl)phenyl)-6,7-di ydro-[l,2,3]thiadiazolo[5,4-c]pyridin- 4(5H)-one; 5-(3-(pentailuoro-16-sulfaneyl)phenyl)-6,7-di ydro-[ l,2,3]thi diazolO[5,4-cJpyri.din- 4(5H)-one; 5-(4-( fluoromelhyl)phenyl)-6,7-di ydro-[l,2,3]thiadiazolo[5,4-c]pyridin-4(5H)- one; 7-bromo-[l,2,3]thiadiazolo[5,4-c]pyridin-4(5H)-one; 5-(4-(trifluoromethyl)phenyl)- [ 1 ,2,3]thiadiazolo[5,4-c]pyridin-4(5H)-one; 5-(3-( 1 , 1 ,2,2-tetrafluoroethoxy)phenyl)-6,7-dihydro- [l,2,3]thiadiazolo[5,4-c]pyridin-4(5H)-one; 4-(difluoromethyl)-N-methyl-N-(2- (trifluoromethyl)benzyl)-l,2,3-thiadiazole-5-carboxamide; 4-(difluoromethyl)-N-(3- fluorobenzyl)-N-methyl-l ,2,3-thiadiazole-5-carboxamide; N-(2-chlorobenzyl)-4- (difluorometliyl)-N-methyl-l,2,3-thiadiazole-5-carboxamide; N-(3,5-difluorobenzyl)-4- (difluoromethyl)-N-methyl-l,2,3-thiadia.zole-5-carboxamide; 4-(difluoromethyl)-N-(2,5- dimethylbenzyl)-N-methyl-l,2,3-thiadiazole-5-carboxaiTiide; 4-(difluoromethyl)-N-(3- (( fluoromethyl)thio)phenyl)-l,2,3-t adiazole-5-carboximidamide 4-(difluoromethyl)-N-(3- (trifluoromethyl)phenyl)- l,2,3-thiadiazole-5-carboxirrddarrdde; 4-(difluoromethyl)-N-(3- (pentafluoro-16-sulfaneyl)phenyl)-l,2,3-t adiazole-5-carboximidamide; 4-(difluoromethyl)-N- (3-fluorophenyl)- l ,2,3-thiadiazole-5-carboximidarnide; N-(3-bromophenyl)-4-(difl.uoromethyl)- l,2,3-thiadiazole-5-carboximidamide;
Claim 5: Use of the Compounds of formula (I) according to claim 1 , 2, 3 or 4 wherein
R1 is selected from halogen, halogenoalkyl selected from -CHC1.2, -CHF2, -C(Rb)F2, .CHF-CF3, - C(Rb)F-€F3, -CF2-CF3,-CHF-CF2-CF3, -CH2F, haloalkoxyalkyl selected from -C(Rb)2OCF3, - C(Rb)2OCHF2, -C(Rb)2OCH2F, -C1-C8-halogenoalkylsulfanyl-C1-C2-alkyl selcted from - C(Rb)2SCF3, "CH(Rb)SCF3, -C(Rb)2SCF2, -CH(Rb)SCF2, Ci-Cs-halogenoalkylsulfinyl-Ci^- alkyl selected from -C(Rb)2SGCF3, ~CH(Rb)SGCF3, -C(Rb)2SOC(Rb)F2, -CH(Rb)SOC(Rb)F2, Ci-C6-alkyl-sulfonate-Ci-C2-alkyl, Ci-Ce-halogenoalkyl-suIfonate-CrC^halogenoalkyl, pentafluoro- ^sulfanyl-d-Cs-aikyl, Ca-Ce-cycloalkyl-Ci-Ca-alkyl, C -C6~cycloalkyl~C¾ -C3- halogenoalkyl, C3-C6-heterocyclyl-Ci-C3-aikyi, C3-C6-heterocyclyI-CrC3-halogerioalkyl;
η
optionally each of these groups may be substituted by one or more groups of R ;
wherein Rb represents, hydrogen, halogen, CrCe-alkyl, Cj-Ce-haioalkyl; and other substitutions as defined in claim 1 ;
for controlling of or preventing against phytopathogenic fungi, bacteria and nematodes of agricultural crops and or horticultural crops.
Claim 6; A composition for controlling or preventing phytopathogenic microorganisms, comprising a compound of formula (I) according to claims 1, 2, 3, or 4 and one or more inert carriers. Claim 7: A composition comprising compound of formula (I) according to claims 1, 2, 3 or 4 and or one or more active compatible compounds selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, nutrients and or mixtures thereof. Claim 8: Compositions according to claims 6 or 7, wherein the concentration of compound of formula. (I) ranges from 1 to 90% by weight with respect to the total weight of the composition, preferably from 5 to 50% by weight with respect to the total weight of the composition.
Claim 9; Use of compound of formula formula (I) according to claims 1 , 2, 3 or 4 or compositions according to any of the claims 6, 7 or 8, for controlling of or preventing against phytopathogenic fungi, insects, bacteria and nematodes of agricultural crops and or horticultural
Claim 10; Use of the compound of formula (I) according to claims 1, 2, 3 or 4, wherein the agricultural crops are cereals, corn, rice, soybean and other leguminous crops, fruit crops, nut crops, citrus crops, any horticultural crops, vegetables crops such as cucurbits, cruciferous, tomato, onions, peppers, potato, oleaginous crops, tobacco, coffee, tea, cacao, sugar beet, sugar cane, cotton, and ornamentals. Claim 11: Use of compound of formula (I) according to claims 1, 2, 3 or 4, or compositions according to any of the claims 6, 7 or 8 for treating seed, wherein the amount of the compound of the formula I, is from 0.1 g to 10 kg per 100 kg of seed.
Claim 12: A method of controlling or preventing infestation of plants with phytopathogenic microorganisms in agricultural crops and or horticultural crops wherein a compound of formula
(I) according to claims 1, 2, 3 or 4, is applied to the plants, to seeds or other parts thereof or the locus thereof.
Claim 13: A method of controlling of or preventing against phytopathogenic microorganisms in agricultural crops and or horticultural crops using the compounds of formula (I) according to claims 1, 2, 3 or 4, or compositions according to any of the claims 6, 7 or 8, which consists in applying effective dosages of compounds or compositions in amounts ranging from 1 g to 5 kg per hectare of agricultural or horticultural crops.
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CN110041324A (en) * 2019-05-17 2019-07-23 南开大学 A kind of thiadiazoles and isothiazole amide derivatives and its preparation method and application
CN111454202A (en) * 2019-01-18 2020-07-28 山东省联合农药工业有限公司 Heteroaryl formanilide compound containing pentafluorothio and preparation method and application thereof
CN111454186A (en) * 2019-01-18 2020-07-28 山东省联合农药工业有限公司 Aryl formanilide compound containing pentafluorothio and preparation method and application thereof

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