US20130291227A1 - Pesticidal compositions and processes related thereto - Google Patents

Pesticidal compositions and processes related thereto Download PDF

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Publication number
US20130291227A1
US20130291227A1 US13/788,736 US201313788736A US2013291227A1 US 20130291227 A1 US20130291227 A1 US 20130291227A1 US 201313788736 A US201313788736 A US 201313788736A US 2013291227 A1 US2013291227 A1 US 2013291227A1
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Prior art keywords
substituted
unsubstituted
methyl
sodium
alkyl
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US13/788,736
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Inventor
Ann M. Buysse
Noormohamed M. Niyaz
Yu Zhang
Martin J. Walsh
Asako Kubota
Ricky Hunter
Tony K. Trullinger
Christian T. Lowe
Daniel Knueppel
David A. Demeter
Akshay Patny
Negar Garizi
Paul Renee LePlae, Jr.
Frank Wessels
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Corteva Agriscience LLC
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Dow AgroSciences LLC
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Priority to US13/788,736 priority Critical patent/US20130291227A1/en
Publication of US20130291227A1 publication Critical patent/US20130291227A1/en
Assigned to DOW AGROSCIENCES LLC reassignment DOW AGROSCIENCES LLC ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BUYSSE, ANN M, DEMETER, DAVID A, GARIZI, NEGAR, HUNTER, RICKY, KNUEPPEL, DANIEL, KUBOTA, Asako, LEPLAE, PAUL R, JR, LOWE, CHRISTIAN T, NIYAZ, NOORMOHAMED M, PATNY, Akshay, TRULLINGER, TONY K, WALSH, MARTIN J, WESSELS, FRANK, ZHANG, YU
Assigned to DOW AGROSCIENCES LLC reassignment DOW AGROSCIENCES LLC ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BUYSSE, ANN M, DEMETER, DAVID A, GARIZI, NEGAR, HUNTER, RICKY, KNUEPPEL, DANIEL, KUBOTA, Asako, LEPLAE, PAUL R, JR, LOWE, CHRISTIAN T, NIYAZ, NOORMOHAMED M, PATNY, Akshay, TRULLINGER, TONY K, WALSH, MARTIN J, WESSELS, FRANK, ZHANG, YU
Priority to US14/816,295 priority patent/US9591857B2/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N43/74—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • 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
    • A01N43/80—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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
    • A01N43/84—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing heterocyclic radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Definitions

  • This disclosure is related to the field of processes to produce molecules that are useful as pesticides (e.g., acaricides, insecticides, molluscicides, and nematicides), such molecules, and processes of using such molecules to control pests.
  • pesticides e.g., acaricides, insecticides, molluscicides, and nematicides
  • Alkenyl means an acyclic, unsaturated (at least one carbon-carbon double bond), branched or unbranched, substituent consisting of carbon and hydrogen, for example, vinyl, allyl, butenyl, pentenyl, and hexenyl.
  • Alkenyloxy means an alkenyl further consisting of a carbon-oxygen single bond, for example, allyloxy, butenyloxy, pentenyloxy, hexenyloxy.
  • Alkoxy means an alkyl further consisting of a carbon-oxygen single bond, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, and tert-butoxy.
  • Alkyl means an acyclic, saturated, branched or unbranched, substituent consisting of carbon and hydrogen, for example, methyl, ethyl, (C 3 )alkyl which represents n-propyl and isopropyl), (C 4 )alkyl which represents n-butyl, sec-butyl, isobutyl, and tert-butyl.
  • Alkynyl means an acyclic, unsaturated (at least one carbon-carbon triple bond), branched or unbranched, substituent consisting of carbon and hydrogen, for example, ethynyl, propargyl, butynyl, and pentynyl.
  • Alkynyloxy means an alkynyl further consisting of a carbon-oxygen single bond, for example, pentynyloxy, hexynyloxy, heptynyloxy, and octynyloxy.
  • Aryl means a cyclic, aromatic substituent consisting of hydrogen and carbon, for example, phenyl, naphthyl, and biphenyl.
  • (C x -C y ) where the subscripts “x” and “y” are integers such as 1, 2, or 3, means the range of carbon atoms for a substituent—for example, (C 1 -C 4 )alkyl means methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl, each individually.
  • “Cycloalkenyl” means a monocyclic or polycyclic, unsaturated (at least one carbon-carbon double bond) substituent consisting of carbon and hydrogen, for example, cyclobutenyl, cyclopentenyl, cyclohexenyl, norbornenyl, bicyclo[2.2.2]octenyl, tetrahydronaphthyl, hexahydronaphthyl, and octahydronaphthyl.
  • Cycloalkenyloxy means a cycloalkenyl further consisting of a carbon-oxygen single bond, for example, cyclobutenyloxy, cyclopentenyloxy, norbornenyloxy, and bicyclo[2.2.2]octenyloxy.
  • Cycloalkyl means a monocyclic or polycyclic, saturated substituent consisting of carbon and hydrogen, for example, cyclopropyl, cyclobutyl, cyclopentyl, norbornyl, bicyclo[2.2.2]octyl, and decahydronaphthyl.
  • Cycloalkoxy means a cycloalkyl further consisting of a carbon-oxygen single bond, for example, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, norbornyloxy, and bicyclo[2.2.2]octyloxy.
  • Halo means fluoro, chloro, bromo, and iodo.
  • Haloalkoxy means an alkoxy further consisting of, from one to the maximum possible number of identical or different, halos, for example, fluoromethoxy, trifluoromethoxy, 2,2-difluoropropoxy, chloromethoxy, trichloromethoxy, 1,1,2,2-tetrafluoroethoxy, and pentafluoroethoxy.
  • Haloalkyl means an alkyl further consisting of, from one to the maximum possible number of, identical or different, halos, for example, fluoromethyl, trifluoromethyl, 2,2-difluoropropyl, chloromethyl, trichloromethyl, and 1,1,2,2-tetrafluoroethyl.
  • Heterocyclyl means a cyclic substituent that may be fully saturated, partially unsaturated, or fully unsaturated, where the cyclic structure contains at least one carbon and at least one heteroatom, where said heteroatom is nitrogen, sulfur, or oxygen. In the case of sulfur, that atom can be in other oxidation states such as a sulfoxide and sulfone.
  • aromatic heterocyclyls include, but are not limited to, benzofuranyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, benzothienyl, benzothiazolyl, cinnolinyl, furanyl, imidazolyl, indazolyl, indolyl, isoindolyl, isoquinolinyl, isothiazolyl, isoxazolyl, oxadiazolyl, oxazolinyl, oxazolyl, phthalazinyl, pyrazinyl, pyrazolinyl, pyrazolyl, pyridazinyl, pyridyl, pyrimidinyl, pyrrolyl, quinazolinyl, quinolinyl, quinoxalinyl, tetrazolyl, thiazolinyl, thiazolyl, thienyl, triaziny
  • Examples of fully saturated heterocyclyls include, but are not limited to, piperazinyl, piperidinyl, morpholinyl, pyrrolidinyl, oxetanyl, tetrahydrofuranyl, tetrahydrothienyl and tetrahydropyranyl.
  • Examples of partially unsaturated heterocyclyls include, but are not limited to, 1,2,3,4-tetrahydroquinolinyl, 4,5-dihydro-oxazolyl, 4,5-dihydro-1H-pyrazolyl, 4,5-dihydro-isoxazolyl, and 2,3-dihydro-[1,3,4]-oxadiazolyl. Additional examples include the following
  • R1 is H, F, Cl, Br, I, CN, NO 2 , substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 2 -C 6 alkenyl, substituted or unsubstituted C 1 -C 6 alkoxy, substituted or unsubstituted C 2 -C 6 alkenyloxy, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 3 -C 10 cycloalkenyl, substituted or unsubstituted C 6 -C 20 aryl, substituted or unsubstituted C 1 -C 20 heterocyclyl, OR9, C( ⁇ X1)R9, C( ⁇ X1)OR9, C( ⁇ X1)N(R9) 2 , N(R9) 2 , N(R9)C( ⁇ X1)R9, S(O) n R9, S(O) n OR9, S(O
  • R2 is H, F, Cl, Br, I, CN, NO 2 , substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 2 -C 6 alkenyl, substituted or unsubstituted C 1 -C 6 alkoxy, substituted or unsubstituted C 2 -C 6 alkenyloxy, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 3 -C 10 cycloalkenyl, substituted or unsubstituted C 6 -C 20 aryl, substituted or unsubstituted C 1 -C 20 heterocyclyl, OR9, C( ⁇ X1)R9, C( ⁇ X1)OR9, C( ⁇ X1)N(R9) 2 , N(R9) 2 , N(R9)C( ⁇ X1)R9, SR9, S(O) n OR9, or R9S(O)
  • R3 is H, F, Cl, Br, I, CN, NO 2 , substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 2 -C 6 alkenyl, substituted or unsubstituted C 1 -C 6 alkoxy, substituted or unsubstituted C 2 -C 6 alkenyloxy, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 3 -C 10 cycloalkenyl, substituted or unsubstituted C 6 -C 20 aryl, substituted or unsubstituted C 1 -C 20 heterocyclyl, OR9, C( ⁇ X1)R9, C( ⁇ X1)OR9, C( ⁇ X1)N(R9) 2 , N(R9) 2 , N(R9)C( ⁇ X1)R9, SR9, S(O) n OR9, or R9S(O)
  • R4 is H, F, Cl, Br, I, CN, NO 2 , substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 2 -C 6 alkenyl, substituted or unsubstituted C 1 -C 6 alkoxy, substituted or unsubstituted C 2 -C 6 alkenyloxy, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 3 -C 10 cycloalkenyl, substituted or unsubstituted C 6 -C 20 aryl, substituted or unsubstituted C 1 -C 20 heterocyclyl, OR9, C( ⁇ X1)R9, C( ⁇ X1)OR9, C( ⁇ X1)N(R9) 2 , N(R9) 2 , N(R9)C( ⁇ X1)R9, SR9, S(O) n OR9, or R9S(
  • R5 is H, F, Cl, Br, I, CN, NO 2 , substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 2 -C 6 alkenyl, substituted or unsubstituted C 1 -C 6 alkoxy, substituted or unsubstituted C 2 -C 6 alkenyloxy, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 3 -C 10 cycloalkenyl, substituted or unsubstituted C 6 -C 20 aryl, OR9, C( ⁇ X1)R9, C( ⁇ X1)OR9, C( ⁇ X1)N(R9) 2 , N(R9) 2 , N(R9)C( ⁇ X1)R9, SR9, S(O) n OR9, or R9S(O) n R9,
  • R7 is O, S, NR9, or NOR9;
  • R8 is substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 2 -C 6 alkenyl, substituted or unsubstituted C 1 -C 6 alkoxy, substituted or unsubstituted C 2 -C 6 alkenyloxy, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 3 -C 10 cycloalkenyl, substituted or unsubstituted C 6 -C 20 aryl, substituted or unsubstituted C 1 -C 20 heterocyclyl, OR9, OR9S(O) n R9, C( ⁇ X1)R9, C( ⁇ X1)OR9, R9C( ⁇ X1)OR9, R9X2C( ⁇ X1)R9X2R9, C( ⁇ X1)N(R9) 2 , N(R9) 2 , N(R9)(R9S(O)
  • R9 is (each independently) H, CN, substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 2 -C 6 alkenyl, substituted or unsubstituted C 1 -C 6 alkoxy, substituted or unsubstituted C 2 -C 6 alkenyloxy, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 3 -C 10 cycloalkenyl, substituted or unsubstituted C 6 -C 20 aryl, substituted or unsubstituted C 1 -C 20 heterocyclyl, substituted or unsubstituted S(O) n C 1 -C 6 alkyl, substituted or unsubstituted N(C 1 -C 6 alkyl) 2 ,
  • (k) n is 0, 1, or 2;
  • X is N or CR n1 where R n1 is H, F, Cl, Br, I, CN, NO 2 , substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 2 -C 6 alkenyl, substituted or unsubstituted C 1 -C 6 alkoxy, substituted or unsubstituted C 2 -C 6 alkenyloxy, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 3 -C 10 cycloalkenyl, substituted or unsubstituted C 6 -C 20 aryl, substituted or unsubstituted C 1 -C 20 heterocyclyl, OR9, C( ⁇ X1)R9, C( ⁇ X1)OR9, C( ⁇ X1)N(R9) 2 , N(R9) 2 , N(R9)C( ⁇ X1)R9, SR9, S(
  • X1 is (each independently) O or S;
  • X2 is (each independently) O, S, ⁇ NR9, or ⁇ NOR9;
  • (O) Z is CN, NO 2 , C 1 -C 6 alkyl(R9), C( ⁇ X1)N(R9) 2 ;
  • R11 is Q 1 (C ⁇ C)R12, wherein Q 1 is a bond, substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 2 -C 6 alkenyl, substituted or unsubstituted C 2 -C 6 alkynyl, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 2 -C 10 cycloalkoxy, substituted or unsubstituted C 1 -C 6 alkylOR9, substituted or unsubstituted C 1 -C 6 alkylS(O) n R9, substituted or unsubstituted C 1 -C 6 alkylS(O) n ( ⁇ NR9), substituted or unsubstituted C 1 -C 6 alkylN(R9) (where (C ⁇ C) is attached directly to the N by a bond), substituted or unsubstituted
  • R12 is Q 1 (except where Q 1 is a bond), F, Cl, Br, I, Si(R9) 3 (where each R9 is independently selected), or R9;
  • A is A1.
  • A is A2.
  • R1 is H.
  • R2 is H.
  • R3 is selected from H, or substituted or unsubstituted C 1 -C 6 alkyl.
  • R3 is selected from H or CH 3 .
  • A1 is A11.
  • R4 is selected from H, or substituted or unsubstituted C 1 -C 6 alkyl, or substituted or unsubstituted C 6 -C 20 aryl.
  • R4 is selected from CH 3 , CH(CH 3 ) 2 , or phenyl.
  • R4 is CH 3 .
  • R4 is selected from H, or substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 2 -C 6 alkenyl, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 6 -C 20 aryl, wherein each said R4, which is substituted, has one or more substituents selected from F, Cl, Br, or I.
  • R4 is H or C 1 -C 6 alkyl.
  • R4 is H, CH 3 , CH 2 CH 3 , CH ⁇ CH 2 , cyclopropyl, CH 2 Cl, CF 3 , or phenyl.
  • R4 is Br or Cl.
  • R5 is H, F, Cl, Br, I, or substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 1 -C 6 alkoxy.
  • R5 is H, OCH 2 CH 3 , F, Cl, Br, or CH 3 .
  • R6 is substituted or unsubstituted C 1 -C 6 alkyl.
  • R6 is selected from is substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 2 -C 6 alkenyl, substituted or unsubstituted C 3 -C 10 cycloalkyl, C( ⁇ X1)R9, C( ⁇ X1)X2R9, R9X2R9, C( ⁇ O)(C 1 -C 6 alkyl)S(O) n (C 1 -C 6 alkyl), (C 1 -C 6 alkyl)OC( ⁇ O)(C 6 -C 20 aryl), (C 1 -C 6 alkyl)OC( ⁇ O)(C 1 -C 6 alkyl), or R9X2C( ⁇ X1)X2R9.
  • R6 and R8 are connected in a cyclic arrangement, where optionally such arrangement can have one or more heteroatoms selected from O, S, or, N, in the cyclic structure connecting R6 and R8.
  • R6 is C 1 -C 6 alkyl, or C 1 -C 6 alkyl-phenyl.
  • R6 is H, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH(CH 3 ) 2 , CH 2 -phenyl, CH 2 CH(CH 3 ) 2 , CH 2 cyclopropyl, C( ⁇ O)CH 2 CH 2 SCH 3 , C( ⁇ O)OC(CH 3 ) 3 , CH 2 CH ⁇ CH 2 , C( ⁇ O)OCH 2 CH 3 , C( ⁇ O)CH(CH 3 )CH 2 SCH 3 , cyclopropyl, CD 3 , CH 2 OC( ⁇ O)phenyl, C( ⁇ O)CH 3 , C( ⁇ O)CH(CH 3 ) 2 , CH 2 C( ⁇ O)CH(CH 3 ) 2 , CH 2 C( ⁇ O)CH 3 , C( ⁇ O)phenyl, CH 2 OCH 3 , CH 2 C( ⁇ O)CH 2 OCH 2 CH 3 , CH 2 CH 2 OCH 3 , CH 2 C( ⁇ O)OCH
  • R6 is methyl or ethyl.
  • R7 is O or S.
  • R8 is selected from substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 2 -C 6 alkenyl, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 6 -C 20 aryl, substituted or unsubstituted C 1 -C 20 heterocyclyl, R9C( ⁇ X1)OR9, SR9, S(O) n OR9, R9S(O) n R9, or R9S(O) n (NZ)R9.
  • R8 is CH(CH 3 )CH 2 SCH 3 , CH(CH 3 ) 2 , C(CH 3 ) 2 CH 2 SCH 3 , CH 2 CH 2 SCH 3 , CH 2 CF 3 , CH 2 CH 2 C( ⁇ O)OCH 3 , N(H)(CH 2 CH 2 SCH 3 ), OCH 2 CH 2 SCH 3 , CH(CH 2 SCH 3 )(CH 2 -phenyl), thiazolyl, oxazolyl, isothiazolyl, substituted-furanyl, CH 3 , C(CH 3 ) 3 , phenyl, CH 2 CH 2 OCH 3 , pyridyl, CH 2 CH(CH 3 )SCH 3 , OC(CH 3 ) 3 , C(CH 3 ) 2 CH 2 SCH 3 , CH(CH 3 )CH(CH 3 )SCH 3 , CH(CH 3 )CF 3 , CH 2 CH 2 -thienyl, CH(CH 3 )
  • R8 is preferably R13—S(O) n —R13 wherein each R13 is independently selected from substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 2 -C 6 alkenyl, substituted or unsubstituted C 1 -C 6 alkoxy, substituted or unsubstituted C 2 -C 6 alkenyloxy, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 3 -C 10 cycloalkenyl, substituted or unsubstituted C 6 -C 20 aryl, substituted or unsubstituted C 1 -C 20 heterocyclyl, substituted or unsubstituted S(O) n C 1 -C 6 alkyl, substituted or unsubstituted N(C 1 -C 6 alkyl) 2 , wherein each said substituted alky
  • R8 is (substituted or unsubstituted C 1 -C 6 alkyl)-S(O) n -(substituted or unsubstituted C 1 -C 6 alkyl) wherein said substituents on said substituted alkyls are independently selected from F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 haloalkyloxy, C 2 -C 6 haloalkenyloxy, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkenyl, C 3 -C 10 halocycloalkyl, C 3 -C 10 halocycloalkenyl, OC 1 -C 6 alkyl, OC 1 -C 6 haloalkyl
  • R8 is selected from CH(CH 3 )SCH 2 CF 3 , CH 2 CH 2 SCH 2 CF 3 , CH 2 SCH 2 CF 3 , CH 2 SCHClCF 3 , CH(CH 2 CH 3 )SCH 2 CF 3 , CH(CH 3 )SCH 2 CHF 2 , CH(CH 3 )SCH 2 CH 2 F, CH 2 CH 2 SCH 2 CH 2 F, CH(CH 3 )S( ⁇ O) 2 CH 2 CF 3 , CH(CH 3 )S( ⁇ O)CH 2 CF 3 , CH(CH 3 )CH 2 SCF 3 , CH(CH 3 )CH 2 SCF 3 , CH(CH 3 )SCH 2 CH 2 CF 3 , and CH 2 CH 2 SCH 2 CH 2 CF 3 .
  • R8 is (substituted or unsubstituted C 1 -C 6 alkyl)-S(O) n -(substituted or unsubstituted C 1 -C 6 alkyl)-(substituted or unsubstituted C 3 -C 10 cycloalkyl) wherein said substituents on said substituted alkyls and said substituted cycloalkyls are independently selected from F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 haloalkyloxy, C 2 -C 6 haloalkenyloxy, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkenyl, C 3 -C 10 halocycloalkyl, C
  • R8 is selected from CH(CH 3 )CH 2 SCH 2 (2,2 difluorocyclopropyl), CH 2 CH 2 SCH 2 (2,2 difluorocyclopropyl), CH 2 CH 2 S( ⁇ O)CH 2 (2,2 difluorocyclopropyl), CH 2 CH 2 S( ⁇ O) 2 CH 2 CH 2 (2,2 difluorocyclopropyl), and CH 2 CH(CF 3 )SCH 2 (2,2 difluorocyclopropyl).
  • R8 is (substituted or unsubstituted C 1 -C 6 alkyl)-S(O) n -(substituted or unsubstituted C 2 -C 6 alkenyl) wherein said substituents on said substituted alkyls and substituted alkenyls are independently selected from F, Cl, Br, I, CN, NO 2 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 haloalkyloxy, C 2 -C 6 haloalkenyloxy, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkenyl, C 3 -C 10 halocycloalkyl, C 3 -C 10 halocycloalkenyl, OC 1 -C 6 alkyl, OC 1
  • R8 is selected from CH 2 CH 2 SCH 2 CH ⁇ CCl 2 , CH 2 SCH 2 CH ⁇ CCl 2 , CH(CH 3 )SCH 2 CH ⁇ CCl 2 , CH(CH 3 )SCH ⁇ CHF, CH 2 CH 2 S( ⁇ O)CH 2 CH 2 CF 3 , and CH 2 CH 2 S( ⁇ O) 2 CH 2 CH 2 CF 3 .
  • X is CR n1 where R n1 is H or halo.
  • X is CR n1 where R n1 is H or F.
  • X1 is O.
  • X2 is O.
  • R11 is substituted or unsubstituted C 1 -C 6 alkylC ⁇ CR12.
  • R11 is CH 2 C ⁇ CH.
  • the molecules of Formula One will generally have a molecular mass of about 100 Daltons to about 1200 Daltons. However, it is generally preferred if the molecular mass is from about 120 Daltons to about 900 Daltons, and it is even more generally preferred if the molecular mass is from about 140 Daltons to about 600 Daltons.
  • step a of Scheme I treatment of a 3-acetopyridine or a 5-acetopyrimidine of Formula II, wherein R1, R2, R3 and X are as previously defined, with carbon disulfide and iodomethane in the presence of a base such as sodium hydride and in a solvent such as dimethyl sulfoxide provides the compound of Formula III.
  • step b of Scheme I the compound of Formula III can be treated with an amine or amine hydrochloride, in the presence of a base, such as triethylamine, in a solvent such as ethyl alcohol to afford the compound of Formula IV, wherein R1, R2, R3, R6 and X are as previously defined.
  • a hydrazine such as methylhydrazine
  • a polar protic solvent such as ethyl alcohol.
  • a boronic acid such as phenylboronic acid
  • a catalyst such as palladium tetrakis
  • a base such as 2M aqueous potassium carbonate
  • a mixed solvent system such as ethanol and toluene
  • a reducing agent such as sodium borohydride
  • a polar protic solvent such as ethanol
  • the compounds of Formula XIIb can be acylated with an acid chloride such as acetyl chloride in a polar aprotic solvent such as dichloromethane using the conditions described in Scheme V.
  • the compounds of Formula XIIb can be treated with benzotriazole and an aldehyde in ethanol followed by reduction using, for example, sodium borohydride, to afford compounds of Formula XIIIa.
  • acylation of compounds of Formula XIIIa in Scheme IV using the conditions described in Scheme IX affords compounds of Formula Ia, wherein R1, R2, R3, R4, R5, R6, R8 and X are as previously defined.
  • step a of Scheme V the compounds of Formula Vc, wherein R1, R2, R3, R4, R5 and R6 and X are as previously defined, can be treated with an acid chloride of Formula XIV, in the presence of a base such as triethylamine or N,N-dimethylaminopyridine in a polar aprotic solvent such as dichloroethane (DCE) to yield compounds of Formula Ib, wherein R8 is as previously defined.
  • a base such as triethylamine or N,N-dimethylaminopyridine
  • a polar aprotic solvent such as dichloroethane (DCE)
  • the 2° amide may be subsequently alkylated in step b of Scheme V with an alkyl halide such as iodoethane, in the presence of a base such as sodium hydride and a polar aprotic solvent such as N,N-dimethylformamide (DMF) to yield the desired compounds of Formula Ib.
  • an alkyl halide such as iodoethane
  • a base such as sodium hydride
  • a polar aprotic solvent such as N,N-dimethylformamide (DMF)
  • a halogen source such as N-chlorosuccinimide or N-bromosuccinimide
  • a polar aprotic solvent such as acetonitrile
  • ureas and carbamates are made from the aminopyrazoles of Formula Ve.
  • Compounds of Formula Ve, wherein X, R1, R2, R3, R4, R5 and R6 are as previously defined are allowed to react with phosgene to provide the intermediate carbamoyl chloride which is subsequently treated with an amine, as shown in step b, or alcohol, as shown in step c, respectively, to generate a urea of Formula Id or a carbamate of Formula Ie, respectively, wherein R9 is as previously defined.
  • step a of Scheme VIII compounds of Formula XIIc, wherein X, R1, R2, R3, R4 and R5 are as previously defined, can be treated with di-tert-butyl dicarbonate (Boc 2 O) and a base such as triethylamine in a polar aprotic solvent such as dichloromethane (DCM) to yield compounds of Formula XVIa.
  • a polar aprotic solvent such as dichloromethane (DCM)
  • compounds of Formula XIIIc can be converted to compounds of Formula Id in the presence of a coupling reagent such as 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl) and a base such as N,N-dimethylaminopyridine (DMAP) in a polar aprotic solvent such as dichloroethane (DCE), as shown in step a.
  • a coupling reagent such as 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl) and a base such as N,N-dimethylaminopyridine (DMAP) in a polar aprotic solvent such as dichloroethane (DCE), as shown in step a.
  • a coupling reagent such as 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride
  • compounds of Formula XIIIc can be converted to compounds of Formula Id in the presence of 2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine in a polar aprotic solvent such as 1,4-dioxane under elevated temperature, as shown in step b.
  • a polar aprotic solvent such as 1,4-dioxane under elevated temperature
  • compounds of Formula XIIIc can be converted to compounds of Formula Id in a polar aprotic solvent such as dichloromethane (DCM), as shown in step c.
  • DCM dichloromethane
  • a thionating agent
  • step a of Scheme X compounds of Formula XIIId, wherein X, R1, R2, R3, R4, R5 and R6 are as previously defined, can be treated with compounds of Formula XIX, wherein R8 is as previously defined, in a polar aprotic solvent such as dichloroethane (DCE) to yield compounds of Formula XX.
  • a polar aprotic solvent such as dichloroethane (DCE)
  • DCE dichloroethane
  • compounds of Formula XX can be treated with a base, such as sodium hydride, in a polar aprotic solvent, such as THF, to yield compounds of Formula XXI, where m is an integer selected from 1, 2, 3, 4, 5, or 6, as shown in step b of Scheme X.
  • the sulfide of Formula XXIIa can be oxidized with an oxidant such as hydrogen peroxide in a polar protic solvent such as hexafluoroisopropanol to give the sulfoxide of Formula XXIII as in step d of Scheme XI.
  • the sulfoxide of Formula XXIII can be further oxidized to the sulfone of Formula XXIV by sodium perborate tetrahydrate in a polar protic solvent such as glacial acetic acid as in step c of Scheme XI.
  • the sulfone of Formula XXIV can be generated in a one-step procedure from the sulfide of Formula XXIIa by using the aforementioned conditions with >2 equivalents of sodium perborate tetrahydrate, as in step b of Scheme XI.
  • the sulfilimine of Formula XXV may be further oxidized to the sulfoximine of Formula XXVI with an oxidant such as meta-Chloroperoxybenzoic acid (“mCPBA”) in the presence of a base such as potassium carbonate in a protic polar solvent system such as ethanol and water as in step b of Scheme XII.
  • an oxidant such as meta-Chloroperoxybenzoic acid (“mCPBA”) in the presence of a base such as potassium carbonate in a protic polar solvent system such as ethanol and water as in step b of Scheme XII.
  • aminopyrazoles of Formula XIIIe can be prepared from iodopyrazoles of Formula XXVII through cross coupling reactions with an appropriate amine in the presence of a base such as cesium carbonate, a copper catalyst such as copper (I) bromide, and a ligand such as 1-(5,6,7,8-tetrahydroquinolin-8-yl)ethanone in a polar aprotic solvent such as DMSO.
  • a base such as cesium carbonate
  • a copper catalyst such as copper (I) bromide
  • a ligand such as 1-(5,6,7,8-tetrahydroquinolin-8-yl)ethanone in a polar aprotic solvent such as DMSO.
  • step a of the Scheme XIV compounds of the formula XXIX, wherein R4 is Cl, R5 is H and X ⁇ represents Cl ⁇ , can be prepared according to the methods described in Acta. Pharm. Suec. 22, 147-156 (1985) by Tolf, Bo-Ragnar and Dahlbom, R.
  • compounds of the Formula XXIX, wherein R4 is Br, X ⁇ represents Br ⁇ and R5 is as defined previously can be prepared by treating compounds of the Formula XXVIII with hydrogen gas in the presence of a metal catalyst such as 5% Pd on alumina and a solution of 50% aqueous HBr in a solvent such as ethanol.
  • step a of Scheme XIV compounds of the Formula XXIX, wherein R4 is Cl or Br, X ⁇ represents Cl ⁇ or Br ⁇ and R5 is as defined previously, can be prepared by treating compounds of the Formula XXVIII, wherein R5 is as defined previously, with a hydrosilane such as triethyl silane in the presence of a metal catalyst such as 5% Pd on alumina and an acid such as HCl or HBr, respectively, in a solvent such as ethanol.
  • a hydrosilane such as triethyl silane
  • a metal catalyst such as 5% Pd on alumina
  • an acid such as HCl or HBr
  • step b of the Scheme XIV compounds of the Formula XXX, wherein R4 is Cl or Br and R5 is as defined previously, can be prepared by treating the compounds of the Formula XXIX, wherein R4 is Cl or Br, X ⁇ represents CF or Br ⁇ and R5 is as defined previously, with di-tert-butyl dicarbonate (Boc 2 O) in the presence of a mixture of solvents such as THF and water and a base such as sodium bicarbonate.
  • a mixture of solvents such as THF and water
  • a base such as sodium bicarbonate
  • step c of the Scheme XIV compounds of the Formula XVIa, wherein X, R1, R2, R3 and R5 are as defined previously and R4 is Cl or Br, preferably Cl can be obtained by treating compounds of the Formula XXX, wherein R4 is Cl or Br and R5 is as defined previously, preferably H, with compounds of the Formula VIIIb, wherein X, R1, R2 and R3 are as defined previously and Q is iodo, in the presence of a catalytic amount of copper salt such as CuCl 2 , a ligand such as an ethane-1,2-diamine derivative such as N 1 ,N 2 -dimethylethane-1,2-diamine and a base such as K 3 PO 4 in a polar aprotic solvent such as acetonitrile at a suitable temperature.
  • a catalytic amount of copper salt such as CuCl 2
  • a ligand such as an ethane-1,2-diamine derivative such as N 1 ,
  • step c pyrazoles of Formula XXX are coupled with compounds of the Formula VIIIb, preferably 3-iodo pyridine, in the presence of a metal catalyst, such as CuCl 2 , and a diamine ligand such as N 1 ,N 2 -dimethylethane-1,2-diamine, and an inorganic base, such as K 3 PO 4 .
  • a metal catalyst such as CuCl 2
  • a diamine ligand such as N 1 ,N 2 -dimethylethane-1,2-diamine
  • an inorganic base such as K 3 PO 4
  • the reaction is carried out in a polar aprotic solvent such as acetonitrile.
  • the reaction is conducted at a temperature from about 60° C. to about 82° C. and preferably from about 75° C. to 82° C.
  • a 1:1.2 molar ratio of pyrazoles of Formula XXX to heterocyclyl iodide of Formula VIIIb may be used, however, a molar ratios of about 5:1 to about 1:5 may also be used.
  • the reaction is conducted at about atmospheric pressure, however, higher or lower pressures can be used.
  • Boc-group of compounds of Formula XVIa can be removed under conditions that are well-known in the art such as under acidic conditions such as TFA in a polar aprotic solvent such as dichloromethane to give compounds of Formula XIId, as shown in step d of Scheme XIV.
  • Bromopyrazoles of Formula XXXI wherein R1, R2, R3, R5, R8 and X are as previously defined, can be allowed to react under Suzuki coupling conditions with a boronic ester such as vinylboronic acid pinacol ester or cyclopropylboronic acid pinacol ester in the presence of a catalyst such as palladium tetrakis, a base such as 2 M aqueous potassium carbonate, and in a mixed solvent system such as ethanol and toluene to provide compounds of Formula XXXII, as shown in step a of Scheme XV.
  • a boronic ester such as vinylboronic acid pinacol ester or cyclopropylboronic acid pinacol ester
  • a catalyst such as palladium tetrakis
  • a base such as 2 M aqueous potassium carbonate
  • a mixed solvent system such as ethanol and toluene
  • the vinyl group of compounds of Formula XXXIII can be reduced in the presence of hydrogen with a catalyst such as 10% Pd/C in a polar protic solvent such methanol to give compounds of Formula XXXIV, as shown in step a of Scheme XVI.
  • a catalyst such as 10% Pd/C in a polar protic solvent such methanol
  • Oxidation of the vinyl group of compounds of Formula XXXIII using an oxidant such as osmium tetroxide in the presence of sodium periodate in mixture of a polar protic solvent such as water and a polar aprotic solvent such as THF gave compounds of Formula XXXV, as shown in step b of Scheme XVI.
  • an ⁇ , ⁇ -unsaturated acid XXXVIII can be treated with a nucleophile such as sodium thiomethoxide in a polar protic solvent such as methanol to give acid XXXIX.
  • a nucleophile such as sodium thiomethoxide
  • a polar protic solvent such as methanol
  • a reagent such as propargyl bromide
  • step a of Scheme XIX compounds of Formula XL, wherein X, R1, R2, R3, R4, R5 and R6 are as previously defined, can be treated with an acid of Formula XLI, wherein R8 is as previously defined, in the presence of a coupling reagent, such as 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl), and a base, such as N,N-dimethylaminopyridine (DMAP), in a polar aprotic solvent, such as dichloromethane (DCM), to yield compounds of Formula XLII.
  • a coupling reagent such as 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl)
  • EDC.HCl 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride
  • DMAP N,
  • step b compounds of the Formula XLII can be treated with a base, such as sodium methoxide, in a polar solvent such as THF, followed by an alkyl halide R9-Hal to give the compounds of the Formula XLIII.
  • a base such as sodium methoxide
  • a polar solvent such as THF
  • step a of Scheme XX compounds of the Formula XL or the corresponding HCl salt, wherein X, R1, R2, R3, R4, R5, and R6 are as previously defined, can be coupled to acids of the formula XLIV, wherein R8 is as previously defined, in the presence of a coupling reagent, such as 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.
  • a coupling reagent such as 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.
  • step b of Scheme XX compounds of the Formula XLV, wherein X, R1, R2, R3, R4, R5, R6 and R8 are as previously defined and Tr represents trityl (triphenylmethyl), can be treated with an acid, such as 2,2,2-trifluoroacetic acid, in the presence of a trialkyl silane, such as triethyl silane, in a polar aprotic solvent, such as methylene chloride, to remove the trityl group to give thiols of the Formula XLVI, wherein X, R1, R2, R3, R4, R5, R6 and R8 are as previously defined.
  • an acid such as 2,2,2-trifluoroacetic acid
  • a trialkyl silane such as triethyl silane
  • a polar aprotic solvent such as methylene chloride
  • thiols of the Formula XLVI can be treated with a base, such as sodium hydride, in a polar aprotic solvent such as tetrahydrofuran, or cesium carbonate in acetonitrile, or DBU in dimethylformamide, and an electrophile (R9-Hal), such as 2-(bromomethyl)-1,1-difluorocyclopropane, in tetrahydrofuran, to give compounds of the Formula XLVII.
  • a base such as sodium hydride
  • a polar aprotic solvent such as tetrahydrofuran, or cesium carbonate in acetonitrile, or DBU in dimethylformamide
  • R9-Hal electrophile
  • 2-(bromomethyl)-1,1-difluorocyclopropane in tetrahydrofuran
  • step a of the Scheme XXI compounds of the Formula XL or the corresponding HCl salt, wherein X, R1, R2, R3, R4, R5, and R6 are as previously defined, can be coupled to acids of the Formula XLVIII, wherein R9 is as previously defined, in the presence of a coupling reagent such as EDC.HCl and a base such as DMAP in a polar aprotic solvent such as DMF to yield compounds of Formula XLIX, where in X, R1, R2, R3, R4, R5, R6 and R9 are as previously defined.
  • a coupling reagent such as EDC.HCl and a base such as DMAP
  • a polar aprotic solvent such as DMF
  • step b of the Scheme XXI compounds of the Formula XLIX, wherein X, R1, R2, R3, R4, R5, R6 and R9 are as previously defined, can be treated with a thio acid salt, such as potassium thioacetate, at an elevated temperature (about 50° C.) in a solvent, such as DMSO, to give compounds of the Formula L, wherein X, R1, R2, R3, R4, R5, R6 and R9 are as previously defined.
  • a thio acid salt such as potassium thioacetate
  • step c of the Scheme XXI compounds of the Formula L, wherein X, R1, R2, R3, R4, R5, R6 and R9 are as previously defined, can be treated with an equimolar amount of a base, such as sodium methoxide, prepared from mixing sodium hydride, and methanol, followed by an electrophile (R9-Halo), such as 2-(bromomethyl)-1,1-difluorocyclopropane, in a solvent, such as tetrahydrofuran, to give compounds of the Formula LI.
  • a base such as sodium methoxide
  • R9-Halo an electrophile
  • step a of Scheme XXII compounds of the Formula XL, wherein X, R1, R2, R3, R4, R5, R6, and halo are as previously defined, can be treated with an acid chloride of Formula LII in the presence of a base, such as triethylamine or diisopropylethylamine in a polar aprotic solvent, such as DCE, to yield compounds of the Formula LII, wherein R8 is either a substituted or unsubstituted alkyl chain.
  • a base such as triethylamine or diisopropylethylamine
  • a polar aprotic solvent such as DCE
  • a one-pot methanolysis/alkylation sequence can be achieved via treatment of compounds of the Formula LIV with one equivalent of a base, such as sodium methoxide (NaOMe) in a polar aprotic solvent, such as tetrahydrofuran (THF).
  • a base such as sodium methoxide (NaOMe)
  • a polar aprotic solvent such as tetrahydrofuran (THF).
  • An alkyl sulfonate or alkyl halide such as 2-iodo-1,1,1-trifluoroethane, can then be added to the reaction mixture to deliver compounds of the Formula LV, wherein R9 is as previously defined.
  • compounds of the Formula LV may be obtained from compounds of the Formula LIII via treatment with an alkyl thiol such as 2,2,2-trifluoroethanethiol at elevated temperatures (about 50° C.) in a polar aprotic solvent, such as THF, in the presence of sodium iodide and a base, such as diisopropylethylamine.
  • a polar aprotic solvent such as THF
  • a base such as diisopropylethylamine
  • step f treating compounds of Formula LIII with an alkyl thiol, such as sodium methanethiolate, in a polar aprotic solvent, such as DMSO, at elevated temperatures (about 50° C.) will afford compounds of Formula LV.
  • step e when compounds of the Formula LIV are treated with two or more equivalents of a base, such as NaOMe, followed by a 1,2,2-trihaloalkyl compound, such as 2-bromo-1,1-difluoroethane, compounds of Formula LVI are obtained.
  • a base such as NaOMe
  • a 1,2,2-trihaloalkyl compound such as 2-bromo-1,1-difluoroethane
  • step a of Scheme 23 compounds of Formula 23.1, wherein X, R1, R2, R3, R4, R5, R6 and R8 are as previously defined, can be treated with a base, such as aqueous 2M lithium hydroxide, in a polar protic solvent, such as methanol, to give compounds of Formula 23.2.
  • a base such as aqueous 2M lithium hydroxide
  • a polar protic solvent such as methanol
  • a base such as sodium hydride
  • a polar aprotic solvent such as tetrahydrofuran (THF)
  • step b of Scheme 24 compounds of Formula 24.2 can be treated with a base, such as triethylamine, and silylation reagents, such as trimethylsilyl trifluoromethanesulfonate and dimethylmethylideneammonium iodide (Eschenmoser's salt) in a polar aprotic solvent, such as dichloromethane (DCM), to yield compounds of Formula 24.3.
  • a base such as triethylamine
  • silylation reagents such as trimethylsilyl trifluoromethanesulfonate and dimethylmethylideneammonium iodide (Eschenmoser's salt)
  • DCM dichloromethane
  • step c of Scheme 24 compounds of Formula 24.3 can be treated with a base, such as potassium hydroxide, and a nucleophile, such as S,S-dimethyl carbonodithioate, in water and a polar aprotic solvent such as tetrahydrofuran (THF) to yield compounds of Formula 24.4, wherein X, R1, R2, R3, R4, R5, R9 and m are as previously defined.
  • a base such as potassium hydroxide
  • a nucleophile such as S,S-dimethyl carbonodithioate
  • step a when compounds of the Formula 25.1, wherein X, R1, R2, R3, R4, R5, R6 and R8 are as previously defined, are treated with two or more equivalents of a base, such as sodium methoxide, followed by a 1,2-dihaloalkyl compound, such as 1-fluoro-2-iodoethane, in a solvent, such as tetrahydrofuran (THF), compounds of Formula 25.2, wherein R9 is as previously defined, are obtained.
  • a base such as sodium methoxide
  • a 1,2-dihaloalkyl compound such as 1-fluoro-2-iodoethane
  • a solvent such as tetrahydrofuran (THF)
  • step a of Scheme 26 An alternative route to vinyl sulfides is described in step a of Scheme 26.
  • This route utilizes conditions developed by Kao and Lee ( Org. Lett. 2011, 13, 5204-5207) in which thiols of the Formula 26.1, wherein X, R1, R2, R3, R4, R5, R6 and R8 are as previously defined, are coupled with a vinyl halide, such as (E)-1-bromo-3,3,3-trifluoroprop-1-ene, in the presence of a catalyst, such as copper(I) oxide, a base, such as potassium hydroxide, and a solvent, such as dioxane, at elevated temperatures to afford products of Formula 26.2, wherein R9 is as previously defined.
  • a catalyst such as copper(I) oxide
  • a base such as potassium hydroxide
  • solvent such as dioxane
  • step a of Scheme 27 an acrylamide of Formula 27.1, wherein X, R1, R2, R3, R4, R5, and R6 are as previously defined, is reacted with a sulfonamide of Formula 27.2, wherein R9 is as previously defined, in the presence of a base, such as potassium carbonate, at elevated temperatures in a polar aprotic solvent, such as dimethylformamide (DMF), to deliver compounds of Formula 27.3.
  • a base such as sodium hydride
  • an alkyl halide such as 2-bromoacetonitrile
  • a polar aprotic solvent such as tetrahydrofuran (THF)
  • Compounds of the Formula 28.3 may be treated with a sulfonyl chloride, such as methanesulfonyl chloride, in the presence of a base, such as diisopropylethylamine, and a polar aprotic solvent, such as dichloromethane (DCM), to afford products of the Formula 28.4, as shown in step b.
  • a sulfonyl chloride such as methanesulfonyl chloride
  • a base such as diisopropylethylamine
  • a polar aprotic solvent such as dichloromethane (DCM)
  • compounds of Formula 28.3 may be prepared via a two step process as described in steps d and e of Scheme 28.
  • Compounds of Formula 28.6 can be converted to compounds of Formula 28.8 when treated with compounds of Formula 28.7 in the presence of a coupling reagent such as 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl) and a base such as N,N-dimethylaminopyridine (DMAP) in a polar aprotic solvent such as dichloroethane (DCE), as shown in step d.
  • a coupling reagent such as 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl) and a base such as N,N-dimethylaminopyridine (DMAP) in a polar aprotic solvent such as dichloroethane (DCE), as shown in step d
  • the Boc-group can be removed under conditions that are well-known in the art, such as under acidic conditions such as trifluoroacetic acid (TFA) in a polar aprotic solvent like dichloromethane to give compounds of Formula 28.3 as in step e.
  • acidic conditions such as trifluoroacetic acid (TFA) in a polar aprotic solvent like dichloromethane to give compounds of Formula 28.3 as in step e.
  • step a of Scheme 29 compounds of Formula 29.1, wherein X, R1, R2, R3, R4, R5, R6 and R8 are as previously defined, can be reacted with either a cyclic or acyclic enone, such as but-3-ene-2-one, under the conditions described by Chakraborti ( Org. Lett. 2006, 8, 2433-2436) to deliver compounds of the Formula 29.2, wherein R9 is as previously defined.
  • a fluorinating reagent such as Deoxo-Fluor®
  • an initiator such as ethanol
  • a polar aprotic solvent such as dichloromethane (DCM)
  • Step a of Scheme 30 depicts the hydrolysis of compounds of the Formula 30.1, wherein X, R1, R2, R3, R4, R5, R6, R8, and R9 are as previously defined, via treatment with an acid, such as aqueous hydrochloric acid, in a solvent, such as THF, to afford an intermediate aldehyde of the Formula 30.2.
  • Compounds of the Formula 30.2 can be immediately reacted with a fluorinating reagent, such as Deoxo-Fluor®, in the presence of an initiator, such as ethanol, and a solvent, such as tetrahydrofuran (THF), to provide products of the Formula 30.3.
  • a fluorinating reagent such as Deoxo-Fluor®
  • a one-pot deprotection/alkylation sequence can be achieved via treatment of compounds of the Formula 31.3 with one equivalent of a base, such as sodium methoxide (NaOMe), in a polar aprotic solvent, such as tetrahydrofuran (THF).
  • a base such as sodium methoxide (NaOMe)
  • a polar aprotic solvent such as tetrahydrofuran (THF).
  • a compound of the Formula 31.4 wherein X, R1, R2, R3, R4, R5, R6, R8 and halo are as previously defined, may then be added to the reaction mixture to afford compounds of the Formula 31.5.
  • a neat mixture of an olefin of the Formula 32.1, where n is an integer selected from 0, 1, 2, 3, 4, or 5, and trimethylsilyl 2,2-difluoro-2-(fluorosulfonyl)acetate can be heated in the presence of sodium fluoride to deliver a substituted difluorocyclopropane of the Formula 32.2, as indicated in step a.
  • this product was treated with tetrabutylammonium fluoride (TBAF) in tetrahydrofuran (THF) to afford an intermediate homoallylic alcohol of the Formula 32.3.
  • TBAF tetrabutylammonium fluoride
  • THF tetrahydrofuran
  • This alcohol was not isolated, but rather immediately treated with p-toluenesulfonyl chloride in the presence of pyridine and dichloromethane to afford a tosylate of the Formula 32.4, as shown in step c.
  • amines of Formula 33.1 are coupled with acid chlorides of Formula 33.2 in the presence of a base, or combination of bases such as pyridine, N,N-dimethylaminopyridine, or diisopropylethylamine.
  • the reaction is carried out in a halogenated solvent such as 1,2-dichloroethane or methylene chloride.
  • the reaction is conducted at a temperature from 0° C. to 80° C. and preferably from about 0° C. to 23° C.
  • a 1:1 molar ratio of the amine of formula 33.1 to acid chloride of Formula 33.2 may be used, however, molar ratios of about 5:1 to about 1:5 may also be used.
  • the reaction is conducted at about atmospheric pressure, however, higher or lower pressures can be used.
  • step a of Scheme 34 the compounds of Formula 34.1, wherein R1, R2, R3, R4, R5 and R6 and X are as previously defined, can be treated with an acid of Formula 34.2, wherein R8 is as previously defined, in the presence of N,N′-dicyclohexylcarbodiimide (DCC), and a base, such as N,N-dimethylaminopyridine (DMAP), in a solvent, such as diethyl ether (Et 2 O), to yield compounds of Formula 34.3.
  • DCC N,N′-dicyclohexylcarbodiimide
  • DMAP N,N-dimethylaminopyridine
  • Et 2 O diethyl ether
  • step a of Scheme 35 aminopyrazoles of Formula 35.1, wherein X, R1, R2, R3, R4, R5 and R6 are as previously defined, can be treated with phosgene and N,N-dimethylaminopyridine (DMAP) at about 80° C. in a polar aprotic solvent such as dichloroethane (DCE).
  • DMAP N,N-dimethylaminopyridine
  • a polar aprotic solvent such as dichloroethane (DCE).
  • DMAP N,N-dimethylaminopyridine
  • DCE dichloroethane
  • step d treatment with an amine, as shown in step b, or an alcohol, as shown in step c, or a thiol, as shown in step d, generates a urea of Formula 35.2, a carbamate of Formula 35.3, or a carbamothioate of Formula 35.4, wherein R9 is as previously defined, respectively.
  • step a of Scheme 36 compounds of Formula 36.1, wherein X, R1, R2 and R3 are as previously defined, can be treated with a base such as triethylamine, carbon disulfide and a sulfonyl chloride such as 4-methylbenzene-1-sulfonyl chloride in a polar aprotic solvent such as tetrahydrofuran (THF) to yield compounds of Formula 36.2.
  • oxazolidin-2-one can be treated with an equimolar amount of a base, such as sodium hydride followed by compounds of Formula 36.2, in a polar aprotic solvent such as dimethylformamide (DMF) to give compounds of the Formula 36.3.
  • the product of step b, (previous to work-up) can be treated with an electrophile such as iodomethane to give compounds of Formula 36.4 as demonstrated in step c of Scheme 36.
  • ureas of Formula 37.1 wherein R1, R2, R3, R4, R5, R6, R8, and X are as previously defined, can be reacted with a base such as lithium bis(trimethylsilyl)amide in a polar aprotic solvent such as THF followed by an acyl chloride such as pivaloyl chloride to yield acylated ureas of Formula 37.2, wherein R1, R2, R3, R4, R5, R6, R8, and X are as previously defined.
  • a base such as lithium bis(trimethylsilyl)amide
  • a polar aprotic solvent such as THF
  • an acyl chloride such as pivaloyl chloride
  • ureas of Formula 37.1 wherein R1, R2, R3, R4, R5, R6, R8, and X are as previously defined, can be reacted with a base such as lithium bis(trimethylsilyl)amide in a polar aprotic solvent such as THF followed by an alkyl halide such as (chloromethyl)(methyl)sulfane to yield alkylated ureas of Formula 37.2, wherein R1, R2, R3, R4, R5, R6, R8, and X are as previously defined.
  • a base such as lithium bis(trimethylsilyl)amide
  • a polar aprotic solvent such as THF
  • an alkyl halide such as (chloromethyl)(methyl)sulfane
  • ureas of Formula 37.1 wherein R1, R2, R3, R4, R5, R6, R8, and X are as previously defined, can be reacted with a base such as lithium bis(trimethylsilyl)amide in a polar aprotic solvent such as THF followed by a sulfonyl chloride such as methanesulfonyl chloride to yield sulfonylated ureas of Formula 37.3, wherein R1, R2, R3, R4, R5, R6, R8, and X are as previously defined.
  • a base such as lithium bis(trimethylsilyl)amide
  • a polar aprotic solvent such as THF
  • a sulfonyl chloride such as methanesulfonyl chloride
  • amines of Formula 38.1 wherein R6 is H or Me, can be reacted with an electrophile of Formula 38.2, wherein R8 and R9 are as previously defined, such as naphthalen-2-ylmethyl 3-(methylthio)propanimidothioate hydrobromide in a polar protic solvent such as ethanol followed by exposure to a base such as MP-Carbonate in a polar protic solvent such as methanol to give amidines of Formula 38.3, wherein R6 is H or Me, and R8 and R9 are as previously defined.
  • step a of the Scheme 39 compounds of the Formula 39.1, wherein X, R1, R2, R3, R4, R5, R6 and R8 are as previously defined, can be treated with alcohols of the Formula 39.2, wherein R9 is as previously defined, in the presence of a base such as sodium hydride or potassium tert-butoxide in a polar aprotic solvent such as THF at appropriate temperatures, to give the corresponding ethers of the Formula 39.3.
  • a base such as sodium hydride or potassium tert-butoxide
  • a polar aprotic solvent such as THF
  • thioethers of the Formula 39.5 can be obtained by treating compounds of the Formula 39.1, wherein X, R1, R2, R3, R4, R5, R6 and R8 are as previously defined, with thiols of the Formula 39.4, wherein R9 is as previously defined, in the presence of a base such as sodium hydride in an aprotic solvent such as THF.
  • step a of Scheme 41 compounds of the Formula 41.1, wherein X, R1, R2, R3, R4, R5 and R6 are as previously defined, can be coupled to acids of the Formula 41.2, wherein R8 and R9 are as previously defined, in the presence of a coupling reagent such as EDC.HCl and a base such as DMAP in an aprotic solvent such as dichloromethane to give phosphonates of the Formula 41.3.
  • a coupling reagent such as EDC.HCl and a base such as DMAP
  • an aprotic solvent such as dichloromethane
  • step b of Scheme 41 phosphonates of the Formula 41.3, wherein X, R1, R2, R3, R4, R5, R6, R8 and R9 are as previously defined, can be treated with carbonyl compounds of the Formula 41.4, where R9 is as previously defined in the presence of a base such as sodium hydride in an aprotic solvent such as THF to give the corresponding alkenes of the Formula 41.5.
  • a base such as sodium hydride
  • an aprotic solvent such as THF
  • step a of the Scheme 42 compounds of the Formula 42.1, wherein X, R1, R2, R3, R4, and R5, are as previously defined, can be treated with trifluoroacetic anhydride in the presence of a base such as triethylamine in an aprotic solvent such as dichloromethane to give amides of the Formula 42.2, where X, R1, R2, R3, R4, and R5, are as previously defined.
  • amides of the Formula 42.2 wherein X, R1, R2, R3, R4, and R5, are as previously defined, can be treated with an alkylating agent such as iodomethane in the presence of a base such as potassium tert-butoxide in a solvent such as THF to afford compounds of the Formula 42.3.
  • a base such as potassium tert-butoxide
  • a solvent such as THF
  • amides of the Formula 42.3, wherein X, R1, R2, R3, R4, and R5, are as previously defined can be treated under basic conditions such as potassium carbonate and methanol to give the corresponding amines of the Formula 42.4.
  • Step 3 Preparation of methyl-(2-methyl-5-pyridin-3-pyrazol-3-yl)-amine
  • N-ethyl-1-methyl-3-(pyridin-3-yl)-1H-pyrazol-5-amine was prepared as described in Example 1, Step 3: ESIMS m/z 203 ([M+H]).
  • N-methyl-1-phenyl-3-(pyridin-3-yl)-1H-pyrazol-5-amine was prepared as described in Example 1, Step 3: ESIMS m/z 252 ([M+2H]).
  • N-(cyclopropylmethyl)-1-methyl-3-(pyridin-3-yl)-1H-pyrazol-5-amine was prepared as described in Example 1, Step 3: ESIMS m/z 230 ([M+2H]).
  • Compound 8 was made in accordance with the procedures disclosed in Example 4 using 2-(methylthio)ethanol in place of 2-methylthioethylamine.
  • Compound 22 was prepared in accordance with the procedures disclosed in Example 15.
  • the reaction which started to slowly exotherm from 35° C. to 55° C. over 2.0 h, was stirred for a total of 16 h and vacuum filtered through a plug of Celite® to give a biphasic mixture.
  • the mixture was transferred to a separatory funnel, the bottom aqueous layer was collected and rotary evaporated (60° C., 50 mmHg) to dryness with the aid of acetonitrile (3 ⁇ 350 mL).
  • the resulting yellow solid was suspended in acetonitrile (150 mL) and allowed to stand for 2 h at room temperature followed by 1 h at 0° C. in the refrigerator.
  • the phases were separated collecting the white gelatinous precipitate and the aqueous layer together.
  • the aqueous was extracted with ethyl acetate (2 ⁇ 200 mL) and the ethyl acetate extracts were combined, washed with brine (200 mL), dried over anhydrous sodium sulfate, filtered and rotary evaporated to give an auburn thick oil (160 g.).
  • the thick oil was suspended in hexane (1000 mL) and stirred at 55° C. for 2 h. This gave a light brown suspension.
  • the mixture was cooled to 0° C. and the solid collected by vacuum filtration and rinsed with hexane (2 ⁇ 10 mL).
  • the mixture was cooled to room temperature and filtered through a bed of Celite®.
  • the filtrate was transferred to a 4 L Erlenmeyer flask equipped with mechanical stirrer and diluted with water until the total volume was about 4 L.
  • the mixture was stirred for 30 minutes at room temperature and the resulting solid was collected by vacuum filtration.
  • the solid was washed with water and washed with water and oven dried for several days in vacuo at 40° C.
  • Compound 172 was also prepared in accordance with the procedures disclosed in Example 13.
  • Compound 317 was prepared in accordance with the procedures disclosed in Example 17 from tert-butyl (3-bromo-1H-pyrazol-4-yl)carbamate and also in accordance with the procedures disclosed in Example 13.
  • HCl 3-Bromo-N-methyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine, HCl was prepared as described in Example 26 from tert-butyl (3-bromo-1-(pyridin-3-yl)-1H-pyrazol-4-yl)(methyl)carbamate (160 mg, 0.45 mmol) in dioxane (1 mL) was added 4M HCl: mp.
  • tert-butyl (3-cyclopropyl-1-(5-fluoropyridin-3-yl)-1H-pyrazol-4-yl)carbamate (705 mg, 2.215 mmol, 71.9% yield) as a yellow solid
  • tert-butyl (1-(5-fluoropyridin-3-yl)-1H-pyrazol-4-yl)carbamate (242 mg, 0.870 mmol, 28.2% yield) as a yellow solid.
  • Compound 369 was prepared in accordance with the procedures disclosed in Example 35.
  • Compound 349 was prepared in accordance with the procedures disclosed in Example 47.
  • Step 1 Preparation of N-(2-((tert-butyldimethylsilyl)oxy)ethyl)-N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-2-methyl-3-(methylthio)propanamide
  • Step 2 Preparation of N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-(2-hydroxyethyl)-2-methyl-3-(methylthio)propanamide (Compound 535)
  • Triethylamine (5.57 mL, 40.00 mmol) and methanesulfonyl chloride (2.85 mL, 36.60 mmol) were sequentially added to a stirred solution of ethyl 1-(hydroxymethyl)cyclopropanecarboxylate (4.80 g, 33.30 mmol) in dichloromethane (83 mL) at 23° C.
  • the resulting bright yellow solution was stirred at 23° C. for 20 h.
  • the reaction mixture was diluted with water and extracted with dichloromethane.
  • 2,2-Dimethyl-3-(methylthio)propanoic acid can be prepared as demonstrated in the literature (reference Musker, W. K.; et al. J. Org. Chem. 1996, 51, 1026-1029).
  • Sodium methanethiolate 1.0 g, 14 mmol, 2.0 equiv
  • 3-chloro-2,2-dimethylpropanoic acid 1.0 g, 7.2 mmol, 1.0 equiv
  • N,N-dimethylformamide 3.0° C.
  • the resulting brown suspension was allowed to warm to 23° C. and stirred for 24 h.
  • Tetrahydro-thiophene-3-carboxylic acid was made using the procedures disclosed in Heterocycles, 2007, 74, 397-409.
  • N,N-dimethylpyridin-4-amine (2.60 g, 21.31 mmol)
  • 2-methyl-3-(tritylthio)propanoic acid (4.41 g, 12.18 mmol)
  • N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (2.36 g, 15.22 mmol) in CH 2 Cl 2 (20 mL) was added 3-chloro-N-ethyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine, 2HCl (3.0 g, 10 mmol).
  • N,N-dimethylpyridin-4-amine (0.82 g, 6.73 mmol) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine, HCl (1.76 g, 9.18 mmol), and the mixture was stirred at room temperature for 16 h. The mixture was diluted with CH 2 Cl 2 (100 mL) and water (50 mL) and the organic phase separated.
  • N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-mercatopropanamide 100 mg, 0.322 mmol
  • sodium hydride 60% dispersion in oil, 13.5 mg, 0.34 mmol
  • the resulting mixture was stirred at room temperature for 10 min followed by addition of 2-(bromomethyl)-1,1-difluorocyclopropane (60 mg, 0.35 mmol).
  • the mixture was stirred at room temperature for 24 h and diluted with saturated aqueous ammonium chloride and ethyl acetate.
  • Molecules 624, 625, 629, 633, 643 653 in Table 1 were made in accordance with the procedures disclosed in Example 89.
  • Molecules 622, 630, 645 in Table 1 were made in accordance with the procedures disclosed in Example 90.
  • the mixture was diluted with saturated aqueous ammonium chloride (5 mL) and ethyl acetate (15 mL), and the organic phase was separated. The aqueous phase was extracted with ethyl acetate (5 mL) and the combined organic phase was washed with brine, dried over MgSO 4 and concentrated in vacuo to give an oily residue.
  • Molecule 651 in Table 1 was made in accordance with the procedures disclosed in Example 96.
  • the mixture was diluted with saturated aqueous NH 4 Cl and ethyl acetate and the organic phase separated.
  • the aqueous phase was extracted with ethyl acetate and the combined organic phase was washed with brine, dried over MgSO 4 and concentrated in vacuo to give a light brown oil.
  • the mixture was diluted with saturated aqueous ammonium chloride (5 mL) and ethyl acetate (15 mL), and the organic phase was separated. The aqueous phase was extracted with ethyl acetate (5 mL) and the combined organic phase was washed with brine, dried over MgSO 4 and concentrated in vacuo to give an oily residue.
  • Molecules 637, 639-642, and 652 in Table 1 were made in accordance with the procedures disclosed in Example 102.
  • reaction was warmed to room temperature and stirred for 30 min. The reaction was again cooled at 0° C. and 2-bromo-1,1-difluoroethane (0.101 mL, 1.275 mmol) in THF (2.1 mL) was added. Reaction was warmed to room temperature and stirred overnight. LC-MS analysis indicated presence of two products, the major corresponding to the desired elimination product and the minor corresponding to the initial alkylation. Therefore, the reaction was cooled to 0° C. and transferred to a vial containing additional NaOMe (freshly prepared by mixing NaH (5.86 mg, 0.147 mmol) and MeOH (5.93 ⁇ L, 0.147 mmol) in THF (0.73 mL) at 0° C.
  • additional NaOMe freshly prepared by mixing NaH (5.86 mg, 0.147 mmol) and MeOH (5.93 ⁇ L, 0.147 mmol
  • reaction was diluted in EtOAc (5 mL) and quenched with H 2 O (5 mL). Aqueous layer was extracted with EtOAc (3 ⁇ 10 mL) and the combined organic extracts were dried over Na 2 SO 4 , filtered, and concentrated in vacuo to give a yellow oil.
  • reaction mixture was concentrated and the crude acid chloride was dissolved in DCM (0.3 mL) which was subsequently added to a pre-stirred solution of 3-chloro-N-methyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine dihydrochloride (0.100 g, 0.355 mmol) and N,N-dimethylpyridin-4-amine (0.130 g, 1.065 mmol) in DCM (1.0 mL) and stirred overnight at room temperature.
  • the reaction mixture was diluted with saturated NaHCO 3 and extracted with DCM. The organic layer was dried over Na 2 SO 4 , filtered and concentrated.

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WO2015106050A1 (en) * 2014-01-10 2015-07-16 Valent Biosciences Corporation (s)-3'-methyl-abscisic acid and esters thereof
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US20190045784A1 (en) * 2016-02-26 2019-02-14 Basf Se Fungicidal mixtures comprising fluxapyroxad
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US20150111737A1 (en) * 2013-10-22 2015-04-23 Dow Agrosciences Llc Synergistic pesticidal compositions and related methods
US9078443B1 (en) 2014-01-31 2015-07-14 Fmc Corporation Methods for controlling weeds using formulations containing fluthiacet-methyl and HPPD herbicides
AR102315A1 (es) * 2014-04-02 2017-02-22 Bayer Cropscience Ag Derivados de pirazolil-nicotin(tio)amida sustituidos y su uso como fungicidas
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WO2016170130A1 (en) * 2015-04-22 2016-10-27 Basf Se Molluscicide and bait composition comprising a molluscicide
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BR102016019512B8 (pt) * 2015-08-26 2022-10-11 Dow Agrosciences Llc Composição compreendendo complexo protetor compreendendo cloquintocet e polímeros ou oligômeros contendo amina, seu método de preparação, e método para controle da vegetação indesejável
RU2018119344A (ru) 2015-10-26 2019-11-28 Байер Кропсайенс Акциенгезельшафт Конденсированные бициклические гетероциклические производные в качестве средства для борьбы с вредителями
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WO2017093214A1 (de) 2015-12-03 2017-06-08 Bayer Cropscience Aktiengesellschaft Mesolonische halogenierte 3-(acetyl)-1-[(1,3-thiazol-5-yl)methyl]-1h-imidazo[1,2-a]pyridin-4-ium-2-olat derivate und verwandte verbindungen als insektizide
CN105503688B (zh) * 2016-01-07 2018-03-13 武汉大学 一种烯烃的卤化三氟甲基化反应的方法
US10681908B2 (en) * 2016-01-25 2020-06-16 Dow Agrosciences Llc Molecules having pesticidal utility, and intermediates, compositions, and processes, related thereto
EP3202267A1 (en) 2016-02-05 2017-08-09 Basf Se Pesticidal mixtures
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RU2018132172A (ru) 2016-02-11 2020-03-11 Байер Кропсайенс Акциенгезельшафт Замещенные 2-оксиимидазолил-карбоксамиды в качестве средств для борьбы с вредителями
EP3416489A1 (en) 2016-02-19 2018-12-26 Basf Se Pesticidally active mixtures comprising anthranilamide compounds
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US11147272B2 (en) 2017-04-10 2021-10-19 Mitsui Chemicals Argro, Inc. Pyridone compounds and agricultural and horticultural fungicides comprising the same as active ingredients
MY190386A (en) 2017-04-11 2022-04-20 Mitsui Chemicals Agro Inc Pyridone compounds and agricultural and horticultural fungicides containing the same as active ingredients
EP3609887A1 (de) 2017-04-12 2020-02-19 Bayer Aktiengesellschaft Mesoionische imidazopyridine als insektizide
US10993439B2 (en) 2017-04-21 2021-05-04 Bayer Aktiengesellschaft Mesoionic imidazopyridines as insecticides
US20200128830A1 (en) 2017-04-24 2020-04-30 Bayer Aktiengesellschaft Fused bicyclic heterocycle derivatives as pesticides
MX2019012803A (es) 2017-04-27 2020-01-23 Bayer Animal Health Gmbh Nuevos derivados de pirazol biciclicos.
TWI782983B (zh) 2017-04-27 2022-11-11 德商拜耳廠股份有限公司 雜芳基苯基胺基喹啉及類似物
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US20200079801A1 (en) 2017-05-03 2020-03-12 Bayer Aktiengesellschaft Trisubstitutedsilylbenzylbenzimidazoles and analogues
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LT3619196T (lt) 2017-05-04 2022-08-10 Bayer Cropscience Aktiengesellschaft 2-{[2-(feniloksimetil)piridin-5-il]oksi}-etanamino dariniai ir susiję junginiai kaip pesticidai, pvz. pasėlių apsaugai
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BR112019028181A2 (pt) 2017-06-30 2020-07-07 Bayer Animal Health Gmbh novos derivados de azaquinolina
WO2019007887A1 (de) 2017-07-06 2019-01-10 Bayer Aktiengesellschaft Insektizide und fungizide wirkstoffkombinationen
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US11254661B2 (en) 2017-08-04 2022-02-22 Bayer Animal Health Gmbh Quinoline derivatives for treating infections with helminths
CN109384728A (zh) * 2017-08-07 2019-02-26 华东理工大学 嘧菌酯通道型溶剂化物及其制备方法
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CN107432281A (zh) * 2017-08-28 2017-12-05 长沙理工大学 一种香石竹矮控剂及其使用方法
CN114591232A (zh) 2017-09-20 2022-06-07 三井化学Agro株式会社 动物用体外寄生虫长效防除剂
BR112020005932A2 (pt) * 2017-09-27 2020-10-06 Arkema Inc. compostos orgânicos funcionalizados com heteroalquenil e heteroalquil halogenados e métodos para preparar tais compostos
CN117430622A (zh) 2017-10-04 2024-01-23 拜耳公司 用作害虫防治剂的杂环化合物的衍生物
EP3473103A1 (de) 2017-10-17 2019-04-24 Bayer AG Wässrige suspensionskonzentrate auf basis von 2-[(2,4-dichlorphenyl)-methyl]-4,4'-dimethyl-3-isoxazolidinon
EP3473100A1 (en) 2017-10-18 2019-04-24 Bayer Aktiengesellschaft Active compound combinations having insecticidal/acaricidal properties
US11819025B2 (en) 2017-10-18 2023-11-21 Bayer Aktiengesellschaft Active compound combinations having insecticidal/acaricidal properties
WO2019076750A1 (en) 2017-10-18 2019-04-25 Bayer Aktiengesellschaft COMBINATIONS OF ACTIVE COMPOUNDS HAVING INSECTICIDE PROPERTIES7ACARICIDES
KR102650038B1 (ko) 2017-10-18 2024-03-22 바이엘 악티엔게젤샤프트 살곤충/살진드기 특성을 갖는 활성 화합물 조합물
CN111246742B (zh) 2017-10-18 2022-09-23 拜耳公司 具有杀虫/杀螨特性的活性化合物结合物
TW201930279A (zh) 2017-10-18 2019-08-01 德商拜耳廠股份有限公司 具有殺昆蟲／殺蟎性質之活性化合物組合（三）
BR112020009446A2 (pt) 2017-11-13 2020-11-03 Bayer Aktiengesellschaft derivados de tetrazólio propila e seu uso como fungicida
WO2019105875A1 (en) 2017-11-28 2019-06-06 Bayer Aktiengesellschaft Heterocyclic compounds as pesticides
WO2019105871A1 (de) 2017-11-29 2019-06-06 Bayer Aktiengesellschaft Stickstoffhaltige heterocyclen als schädlingsbekämpfungsmittel
TW201927768A (zh) 2017-12-21 2019-07-16 德商拜耳廠股份有限公司 三取代矽基甲基雜芳氧基喹啉及類似物
EP3305786A3 (de) 2018-01-22 2018-07-25 Bayer CropScience Aktiengesellschaft Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel
CN111836802A (zh) 2018-02-12 2020-10-27 拜耳公司 杀真菌的*二唑
WO2019162228A1 (en) 2018-02-21 2019-08-29 Bayer Aktiengesellschaft 1-(5-substituted imidazol-1-yl)but-3-en derivatives and their use as fungicides
KR20200122353A (ko) 2018-02-21 2020-10-27 바이엘 악티엔게젤샤프트 해충 방제제로서의 축합 바이시클릭 헤테로시클릭 유도체
WO2019170626A1 (en) 2018-03-08 2019-09-12 Bayer Aktiengesellschaft Use of heteroaryl-triazole and heteroaryl-tetrazole compounds as pesticides in plant protection
CN111836815A (zh) 2018-03-12 2020-10-27 拜耳公司 作为害虫防治剂的稠合双环杂环衍生物
CA3096497A1 (en) 2018-04-10 2019-10-17 Bayer Aktiengesellschaft Oxadiazoline derivatives
AU2019250361B2 (en) 2018-04-12 2023-03-23 Bayer Aktiengesellschaft Heteroaryl-triazole compounds as pesticides
US12089597B2 (en) 2018-04-13 2024-09-17 Bayer Aktiengesellschaft Active ingredient combinations with insecticidal, nematicidal and acaricidal properties
WO2019197615A1 (de) 2018-04-13 2019-10-17 Bayer Aktiengesellschaft Wirkstoffkombinationen mit fungiziden, insektiziden und akariziden eigenschaften
UY38184A (es) 2018-04-17 2019-10-31 Bayer Ag Compuestos heteroarilo-triazol y heteroarilo-tetrazol novedosos como plaguicidas
BR112020019854A2 (pt) 2018-04-20 2021-01-05 Bayer Aktiengesellschaft Compostos de heteroaril-triazol e heteroaril-tetrazol como pesticidas
KR20210005081A (ko) 2018-04-20 2021-01-13 바이엘 악티엔게젤샤프트 해충 방제제로서의 헤테로시클렌 유도체
AU2019260016B2 (en) 2018-04-25 2022-11-17 Bayer Aktiengesellschaft Novel heteroaryl-triazole and heteroaryl-tetrazole compounds as pesticides
WO2019215182A1 (en) 2018-05-09 2019-11-14 Bayer Animal Health Gmbh New quinoline derivatives
WO2019224143A1 (de) 2018-05-24 2019-11-28 Bayer Aktiengesellschaft Wirkstoffkombinationen mit insektiziden, nematiziden und akariziden eigenschaften
BR112020026556A2 (pt) 2018-06-25 2021-03-23 Bayer Cropscience Lp Método de tratamento de semente
AU2019296166B2 (en) 2018-06-26 2024-01-18 Bayer Aktiengesellschaft Heterocyclene derivatives as pest control agents
WO2020002189A1 (de) 2018-06-27 2020-01-02 Bayer Aktiengesellschaft Wirkstoffkombinationen
EP3586630A1 (en) 2018-06-28 2020-01-01 Bayer AG Active compound combinations having insecticidal/acaricidal properties
MA53086A (fr) 2018-07-05 2021-10-13 Bayer Ag Thiophènecarboxamides et analogues substitués utilisés en tant qu'agents antibactériens
WO2020020813A1 (en) 2018-07-25 2020-01-30 Bayer Aktiengesellschaft Fungicidal active compound combinations
TWI828725B (zh) 2018-07-25 2024-01-11 日商三井化學植保股份有限公司 吡啶酮化合物及以吡啶酮化合物作為有效成分的農園藝用殺菌劑
WO2020020816A1 (en) 2018-07-26 2020-01-30 Bayer Aktiengesellschaft Novel triazole derivatives
BR112021001477A2 (pt) 2018-07-27 2021-05-11 Bayer Aktiengesellschaft formulações de liberação controlada para agroquímicos
AU2019313545A1 (en) 2018-07-31 2021-02-25 Bayer Aktiengesellschaft Controlled release formulations with lignin for agrochemicals
WO2020043650A1 (en) 2018-08-29 2020-03-05 Bayer Aktiengesellschaft Active compound combinations having insecticidal/acaricidal properties
BR112021003665A2 (pt) 2018-09-13 2021-05-18 Bayer Aktiengesellschaft derivados de heterocicleno como agentes de controle de pragas
CN112714614A (zh) 2018-09-17 2021-04-27 拜耳公司 杀真菌剂异氟普仑用于在谷物中防治麦角菌和减少菌核的用途
WO2020070050A1 (en) 2018-10-01 2020-04-09 Bayer Aktiengesellschaft Fungicidal 5-substituted imidazol-1-yl carbinol derivatives
EP3636644A1 (de) 2018-10-11 2020-04-15 Bayer Aktiengesellschaft Mesoionische imidazopyridine als insektizide
WO2020078839A1 (de) 2018-10-16 2020-04-23 Bayer Aktiengesellschaft Wirkstoffkombinationen
JP2022512719A (ja) 2018-10-18 2022-02-07 バイエル・アクチエンゲゼルシヤフト ピリジルフェニルアミノキノリン類及び類似体
MX2021004448A (es) 2018-10-18 2021-07-07 Bayer Ag Heteroarilaminoquinolinas y analogos.
TW202028193A (zh) 2018-10-20 2020-08-01 德商拜耳廠股份有限公司 氧雜環丁基苯氧基喹啉及類似物
EP3643711A1 (en) 2018-10-24 2020-04-29 Bayer Animal Health GmbH New anthelmintic compounds
CN109769807B9 (zh) * 2018-11-14 2021-02-09 浙江农林大学 一种具有双分子结构的缓释灭藻微胶囊及其制备方法
AR117169A1 (es) 2018-11-28 2021-07-14 Bayer Ag (tio)amidas de piridazina como compuestos fungicidas
CA3122156A1 (en) 2018-12-07 2020-06-11 Bayer Aktiengesellschaft Herbicidal compositions
US20220053762A1 (en) 2018-12-07 2022-02-24 Bayer Aktiengesellschaft Herbicidal compositions
EP3620052A1 (en) 2018-12-12 2020-03-11 Bayer Aktiengesellschaft Use of phenoxypyridinyl-substituted (1h-1,2,4-triazol-1-yl)alcohols for controlling fungicidal diseases in maize
CN109369617B (zh) * 2018-12-13 2020-07-31 中国科学院福建物质结构研究所 一种1-(2-吡啶基)-吡唑-3-甲酸及其衍生物的合成方法
WO2020126980A1 (en) 2018-12-18 2020-06-25 Bayer Aktiengesellschaft Active compound combinations having insecticidal/acaricidal properties
AR117461A1 (es) 2018-12-20 2021-08-04 Bayer Ag Compuestos de heterociclil piridazina como fungicidas
BR112021009908A2 (pt) 2018-12-21 2021-08-17 Bayer Aktiengesellschaft 1,3,4-oxadiazóis e derivados dos mesmos como novos agentes antifúngicos
EP3669652A1 (en) 2018-12-21 2020-06-24 Bayer AG Active compound combination
EP3679790A1 (en) 2019-01-08 2020-07-15 Bayer AG Active compound combinations
EP3679793A1 (en) 2019-01-08 2020-07-15 Bayer AG Active compound combinations
EP3679791A1 (en) 2019-01-08 2020-07-15 Bayer AG Active compound combinations
EP3679792A1 (en) 2019-01-08 2020-07-15 Bayer AG Active compound combinations
EP3679789A1 (en) 2019-01-08 2020-07-15 Bayer AG Active compound combinations
EP3545764A1 (en) 2019-02-12 2019-10-02 Bayer AG Crystal form of 2-({2-fluoro-4-methyl-5-[(r)-(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2- trifluoroethyl)-1,3-thiazolidin-4-one
AU2020229979A1 (en) 2019-02-26 2021-09-02 Bayer Aktiengesellschaft Fused bicyclic heterocycle derivatives as pesticides
BR112021010400A2 (pt) 2019-02-26 2021-08-24 Bayer Aktiengesellschaft Derivados heterocíclicos bicíclicos condensados como agentes de controle de praga
BR112021009703A2 (pt) 2019-03-01 2021-11-23 Bayer Ag Combinações de compostos ativos tendo propriedades inseticidas/acaricidas
AR118247A1 (es) 2019-03-05 2021-09-22 Bayer Ag Combinación de compuestos activos
WO2020182929A1 (en) 2019-03-13 2020-09-17 Bayer Aktiengesellschaft Substituted ureas and derivatives as new antifungal agents
EP3937639A1 (en) 2019-03-15 2022-01-19 Bayer Aktiengesellschaft Active compound combinations having insecticidal/acaricidal properties
EP3564225A1 (en) 2019-03-21 2019-11-06 Bayer Aktiengesellschaft Crystalline form of spiromesifen
EP3725788A1 (en) 2019-04-15 2020-10-21 Bayer AG Novel heteroaryl-substituted aminoalkyl azole compounds as pesticides
CN114007420A (zh) 2019-05-08 2022-02-01 拜耳公司 用于杀真菌剂的高扩散性ulv制剂
EP3965576A1 (en) 2019-05-08 2022-03-16 Bayer Aktiengesellschaft Active compound combination
EP3965575A1 (en) 2019-05-10 2022-03-16 Bayer CropScience LP Active compound combinations
WO2020229398A1 (de) 2019-05-14 2020-11-19 Bayer Aktiengesellschaft (1-alkenyl)-substituierte pyrazole und triazole als schädlingsbekämpfungsmittel
EP3750888A1 (en) 2019-06-12 2020-12-16 Bayer Aktiengesellschaft Crystalline form a of 1,4-dimethyl-2-[2-(pyridin-3-yl)-2h-indazol-5-yl]-1,2,4-triazolidine-3,5-dione
BR112021025300A2 (pt) 2019-06-21 2022-02-01 Bayer Ag Oxadiazóis fungicidas
BR112021025865A2 (pt) 2019-06-21 2022-03-03 Bayer Ag Hidróxi-isoxazolinas e derivados das mesmas
EP3986877A1 (en) 2019-06-21 2022-04-27 Bayer Aktiengesellschaft Hydroxyisoxazolines and derivatives thereof
BR112021025333A2 (pt) 2019-06-21 2022-05-24 Bayer Ag Benzilfenil hidróxi-isoxazolinas e análogos como novos agentes antifúngicos
EP3986891A1 (en) 2019-06-21 2022-04-27 Bayer Aktiengesellschaft Hydroxyisoxazolines and derivatives thereof
WO2020254493A1 (en) 2019-06-21 2020-12-24 Bayer Aktiengesellschaft Thienylhydroxyisoxazolines and derivatives thereof
EP3986875A1 (en) 2019-06-21 2022-04-27 Bayer Aktiengesellschaft Phenoxyphenyl hydroxyisoxazolines and analogues as new antifungal agents
EP3986892A1 (en) 2019-06-21 2022-04-27 Bayer Aktiengesellschaft Hydroxyisoxazolines and use thereof as fungicides
AR119228A1 (es) 2019-06-24 2021-12-01 Bayer Cropscience Lp Una cepa de bacilo y métodos para su utilización en la promoción del crecimiento de las plantas
EP3608311A1 (en) 2019-06-28 2020-02-12 Bayer AG Crystalline form a of n-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-4-methylsulfonyl-5-(1,1,2,2,2-pentafluoroethyl)pyrazole-3-carboxamide
EP3994130B1 (en) 2019-07-03 2024-07-10 Bayer Aktiengesellschaft Substituted thiophene carboxamides and derivatives thereof as microbicides
CN114340393B (zh) 2019-07-04 2024-05-24 拜耳公司 除草组合物
MX2022000950A (es) 2019-07-22 2022-02-14 Bayer Ag 5-amino pirazoles y triazoles como plaguicidas.
CA3148211A1 (en) * 2019-07-22 2021-01-28 University Of Hawaii Aryl sulfonamides as small molecule stat3 inhibitors
US20220274947A1 (en) 2019-07-23 2022-09-01 Bayer Aktiengesellschaft Novel heteroaryl-triazole compounds as pesticides
MX2022000951A (es) 2019-07-23 2022-02-14 Bayer Ag Novedosos compuestos de heteroaril-triazol como plaguicidas.
TW202120490A (zh) 2019-07-30 2021-06-01 德商拜耳動物保健有限公司 新穎異喹啉衍生物
EP3771714A1 (de) 2019-07-30 2021-02-03 Bayer AG Stickstoffhaltige heterocyclen als schädlingsbekämpfungsmittel
EP3701796A1 (en) 2019-08-08 2020-09-02 Bayer AG Active compound combinations
CN114615891A (zh) 2019-09-11 2022-06-10 拜耳公司 基于2-[(2,4-二氯苯基)甲基]-4,4’-二甲基-3-异噁唑烷酮和苗前除草剂的高效制剂
US20220403410A1 (en) 2019-09-26 2022-12-22 Bayer Aktiengesellschaft Rnai-mediated pest control
KR20220079905A (ko) 2019-10-09 2022-06-14 바이엘 악티엔게젤샤프트 살충제로서의 신규 헤테로아릴-트리아졸 화합물
AU2020363864A1 (en) 2019-10-09 2022-04-21 Bayer Aktiengesellschaft Novel heteroaryl-triazole compounds as pesticides
TW202128650A (zh) 2019-10-11 2021-08-01 德商拜耳動物保健有限公司 作為殺蟲劑之新穎的雜芳基取代之吡𠯤衍生物
CN110672753B (zh) * 2019-11-04 2022-05-20 青海省农林科学院 一种氟咯草酮异构体的拆分和检测方法
EP4055010A1 (de) 2019-11-07 2022-09-14 Bayer Aktiengesellschaft Substituierte sulfonylamide zur bekämpfung tierischer schädlinge
WO2021097162A1 (en) 2019-11-13 2021-05-20 Bayer Cropscience Lp Beneficial combinations with paenibacillus
TW202134226A (zh) 2019-11-18 2021-09-16 德商拜耳廠股份有限公司 作為殺蟲劑之新穎雜芳基-三唑化合物
TW202136248A (zh) 2019-11-25 2021-10-01 德商拜耳廠股份有限公司 作為殺蟲劑之新穎雜芳基-三唑化合物
WO2021122986A1 (en) 2019-12-20 2021-06-24 Bayer Aktiengesellschaft Thienyloxazolones and analogues
US20230046892A1 (en) 2019-12-20 2023-02-16 Bayer Aktiengesellschaft Substituted thiophene carboxamides, thiophene carboxylic acids and derivatives thereof
EP3845304A1 (en) 2019-12-30 2021-07-07 Bayer AG Capsule suspension concentrates based on polyisocyanates and biodegradable amine based cross-linker
WO2021165195A1 (en) 2020-02-18 2021-08-26 Bayer Aktiengesellschaft Heteroaryl-triazole compounds as pesticides
EP3868207A1 (de) 2020-02-24 2021-08-25 Bayer Aktiengesellschaft Verkapselte pyrethroide mit verbesserter wirksamkeit bei boden- und blattanwendungen
EP3708565A1 (en) 2020-03-04 2020-09-16 Bayer AG Pyrimidinyloxyphenylamidines and the use thereof as fungicides
AU2021253168A1 (en) 2020-04-09 2022-11-03 Elanco Animal Health Gmbh Substituted condensed azines as anthelmintic compounds
BR112022020704A2 (pt) 2020-04-16 2022-11-29 Bayer Ag Combinações de compostos ativos e composições fungicidas compreendendo os mesmos
AR122415A1 (es) 2020-04-16 2022-09-07 Bayer Ag Combinaciones de compuestos activos y composiciones fungicidas que los comprenden
WO2021209366A1 (en) 2020-04-16 2021-10-21 Bayer Aktiengesellschaft Active compound combinations and fungicide compositions comprising those
BR112022020774A2 (pt) 2020-04-16 2022-11-29 Bayer Ag Combinações de compostos ativos e composições fungicidas compreendendo as mesmas
WO2021209490A1 (en) 2020-04-16 2021-10-21 Bayer Aktiengesellschaft Cyclaminephenylaminoquinolines as fungicides
BR112022020792A2 (pt) 2020-04-16 2022-11-29 Bayer Ag Combinações de compostos ativos e composições fungicidas compreendendo-as
AU2021260029A1 (en) 2020-04-21 2022-11-24 Bayer Aktiengesellschaft 2-(het)aryl-substituted condensed heterocyclic derivatives as pest control agents
JP2023538713A (ja) 2020-05-06 2023-09-11 バイエル、アクチエンゲゼルシャフト 殺真菌性化合物としてのピリジン（チオ）アミド
TW202208347A (zh) 2020-05-06 2022-03-01 德商拜耳廠股份有限公司 作為殺蟲劑之新穎雜芳基三唑化合物
JP2023525349A (ja) 2020-05-12 2023-06-15 バイエル、アクチエンゲゼルシャフト 殺真菌性化合物としてのトリアジンおよびピリミジン（チオ）アミド化合物
BR112022023550A2 (pt) 2020-05-19 2023-01-03 Bayer Cropscience Ag (tio)amidas azabicíclicas como compostos fungicidas
CN115803320A (zh) 2020-06-04 2023-03-14 拜耳公司 作为新的杀真菌剂的杂环基嘧啶类和杂环基三嗪类
WO2021249995A1 (en) 2020-06-10 2021-12-16 Bayer Aktiengesellschaft Azabicyclyl-substituted heterocycles as fungicides
KR20230026388A (ko) 2020-06-18 2023-02-24 바이엘 악티엔게젤샤프트 작물 보호를 위한 살진균제로서의 3-(피리다진-4-일)-5,6-디히드로-4h-1,2,4-옥사디아진 유도체
UY39275A (es) 2020-06-19 2022-01-31 Bayer Ag 1,3,4-oxadiazol pirimidinas como fungicidas, procesos e intermediarios para su preparación, métodos de uso y usos de los mismos
UY39276A (es) 2020-06-19 2022-01-31 Bayer Ag Uso de compuestos de 1,3,4–oxadiazol–2–ilpirimidina para controlar microorganismos fitopatógenos, métodos de uso y composiciones.
BR112022025710A2 (pt) 2020-06-19 2023-03-07 Bayer Ag 1,3,4-oxadiazol pirimidinas e 1,3,4-oxadiazol piridinas como fungicidas
WO2021255091A1 (en) 2020-06-19 2021-12-23 Bayer Aktiengesellschaft 1,3,4-oxadiazoles and their derivatives as fungicides
EP3929189A1 (en) 2020-06-25 2021-12-29 Bayer Animal Health GmbH Novel heteroaryl-substituted pyrazine derivatives as pesticides
BR112022026484A2 (pt) 2020-06-26 2023-01-31 Bayer Ag Concentrados de suspensão de cápsula aquosa compreendendo grupos éster biodegradáveis
JP2023532548A (ja) 2020-07-02 2023-07-28 バイエル・アクチエンゲゼルシヤフト 有害生物防除剤としてのヘテロサイクレン誘導体
WO2022033991A1 (de) 2020-08-13 2022-02-17 Bayer Aktiengesellschaft 5-amino substituierte triazole als schädlingsbekämpfungsmittel
WO2022053453A1 (de) 2020-09-09 2022-03-17 Bayer Aktiengesellschaft Azolcarboxamide als schädlingsbekämpfungsmittel
WO2022058327A1 (en) 2020-09-15 2022-03-24 Bayer Aktiengesellschaft Substituted ureas and derivatives as new antifungal agents
EP3974414A1 (de) 2020-09-25 2022-03-30 Bayer AG 5-amino substituierte pyrazole und triazole als schädlingsbekämpfungsmittel
EP3915371A1 (en) 2020-11-04 2021-12-01 Bayer AG Active compound combinations and fungicide compositions comprising those
CN114442601B (zh) * 2020-11-06 2024-06-18 宇通客车股份有限公司 一种无人驾驶车辆跟踪控制方法及装置
EP3994985A1 (en) 2020-11-08 2022-05-11 Bayer Aktiengesellschaft Agrochemical composition with improved drift properties
EP3994987A1 (en) 2020-11-08 2022-05-11 Bayer AG Agrochemical composition with improved drift and uptake properties
EP3994995A1 (en) 2020-11-08 2022-05-11 Bayer Aktiengesellschaft Low drift, rainfastness, high spreading, high uptake and ulv tank mix adjuvant formulation
EP3994994A1 (en) 2020-11-08 2022-05-11 Bayer Aktiengesellschaft Low drift, rainfastness, high spreading, high uptake and ulv tank mix adjuvant formulation
EP3994986A1 (en) 2020-11-08 2022-05-11 Bayer Aktiengesellschaft Agrochemical composition with improved drift and spreading properties
EP3994988A1 (en) 2020-11-08 2022-05-11 Bayer AG Agrochemical composition with improved drift, spreading and rainfastness properties
EP3994992A1 (en) 2020-11-08 2022-05-11 Bayer AG Low drift, rainfastness, high uptake and ulv tank mix adjuvant formulation
EP3994990A1 (en) 2020-11-08 2022-05-11 Bayer AG Agrochemical composition with improved drift, spreading and uptake properties
EP3994993A1 (en) 2020-11-08 2022-05-11 Bayer Aktiengesellschaft Low drift, rainfastness, high spreading and ulv tank mix adjuvant formulation
EP3994989A1 (en) 2020-11-08 2022-05-11 Bayer AG Agrochemical composition with improved drift, rainfastness and uptake properties
EP3994991A1 (en) 2020-11-08 2022-05-11 Bayer Aktiengesellschaft Agrochemical composition with improved drift, spreading, uptake and rainfastness properties
EP3915971A1 (en) 2020-12-16 2021-12-01 Bayer Aktiengesellschaft Phenyl-s(o)n-phenylamidines and the use thereof as fungicides
WO2022129190A1 (en) 2020-12-18 2022-06-23 Bayer Aktiengesellschaft (hetero)aryl substituted 1,2,4-oxadiazoles as fungicides
WO2022129196A1 (en) 2020-12-18 2022-06-23 Bayer Aktiengesellschaft Heterobicycle substituted 1,2,4-oxadiazoles as fungicides
WO2022129188A1 (en) 2020-12-18 2022-06-23 Bayer Aktiengesellschaft 1,2,4-oxadiazol-3-yl pyrimidines as fungicides
WO2022152728A1 (de) 2021-01-15 2022-07-21 Bayer Aktiengesellschaft Herbizide zusammensetzungen
EP4036083A1 (de) 2021-02-02 2022-08-03 Bayer Aktiengesellschaft 5-oxy substituierte hetereozyklen, als schädlingsbekämpfungsmittel
EP4294187A1 (en) 2021-02-19 2023-12-27 Syngenta Crop Protection AG Insect and acarina pest control
WO2022200364A1 (en) 2021-03-25 2022-09-29 Syngenta Crop Protection Ag Insect, acarina and nematode pest control
WO2022207496A1 (en) 2021-03-30 2022-10-06 Bayer Aktiengesellschaft 3-(hetero)aryl-5-chlorodifluoromethyl-1,2,4-oxadiazole as fungicide
WO2022207494A1 (en) 2021-03-30 2022-10-06 Bayer Aktiengesellschaft 3-(hetero)aryl-5-chlorodifluoromethyl-1,2,4-oxadiazole as fungicide
CN117597344A (zh) 2021-05-06 2024-02-23 拜耳公司 烷基酰胺取代的环状咪唑及其作为杀虫剂的用途
WO2022238194A1 (de) 2021-05-10 2022-11-17 Bayer Aktiengesellschaft Herbizid/safener-kombinationen basierend auf safenern aus der klasse der substituierten [(1,5-diphenyl1h-1,2,4-triazol-3-yl)oxy]essigsäuren sowie deren salze
EP4337661A1 (de) 2021-05-12 2024-03-20 Bayer Aktiengesellschaft 2-(het)aryl-substituierte kondensierte heterocyclen-derivate als schädlingsbekämpfungsmittel
JP2024529148A (ja) 2021-08-13 2024-08-01 バイエル、アクチエンゲゼルシャフト 活性化合物組合せおよびこれらを含む抗真菌剤組成物
CN118103364A (zh) 2021-08-25 2024-05-28 拜耳公司 作为农药的新的吡嗪基-三唑化合物
EP4144739A1 (de) 2021-09-02 2023-03-08 Bayer Aktiengesellschaft Anellierte pyrazole als schädlingsbekämpfungsmittel
EP4148052A1 (en) 2021-09-09 2023-03-15 Bayer Animal Health GmbH New quinoline derivatives
WO2023078915A1 (en) 2021-11-03 2023-05-11 Bayer Aktiengesellschaft Bis(hetero)aryl thioether (thio)amides as fungicidal compounds
WO2023092050A1 (en) 2021-11-20 2023-05-25 Bayer Cropscience Lp Beneficial combinations with recombinant bacillus cells expressing a serine protease
WO2023099445A1 (en) 2021-11-30 2023-06-08 Bayer Aktiengesellschaft Bis(hetero)aryl thioether oxadiazines as fungicidal compounds
CA3242421A1 (en) 2021-12-15 2023-06-22 Bayer Aktiengesellschaft Spectroscopic solution for non-destructive quantification of one or more chemical substances in a matrix comprising coating and bulk material in a sample, such as coated seeds, using multivariate data analysis
IL314174A (en) 2022-01-14 2024-09-01 Enko Chem Inc Protoporphyrinogen oxidase inhibitors
CN114768545B (zh) * 2022-03-31 2023-11-10 青岛吉景新型材料有限公司 硝酸纤维素微孔膜及其连续制备方法
AU2023258006A1 (en) 2022-04-18 2024-10-31 Basf Corporation High-load agricultural formulations and methods of making same
EP4265110A1 (en) 2022-04-20 2023-10-25 Bayer AG Water dispersible granules with low melting active ingredients prepared by extrusion
CN114808175B (zh) * 2022-04-28 2024-05-17 汕头市鼎泰丰实业有限公司 一种抗菌除虫面料及其制备方法
WO2023213670A1 (en) 2022-05-03 2023-11-09 Bayer Aktiengesellschaft Crystalline forms of (5s)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4h-1,2,4-oxadiazine
WO2023213626A1 (en) 2022-05-03 2023-11-09 Bayer Aktiengesellschaft Use of (5s)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4h-1,2,4-oxadiazine for controlling unwanted microorganisms
WO2023217619A1 (en) 2022-05-07 2023-11-16 Bayer Aktiengesellschaft Low drift aqueous liquid formulations for low, medium, and high spray volume application
WO2023237444A1 (en) 2022-06-06 2023-12-14 Bayer Aktiengesellschaft Agrochemical formulations comprising crystalline form a of 4-[(6-chloro-3-pyridylmethyl)(2,2-difluoroethyl)amino]furan-2(5h)-one
EP4295683A1 (en) 2022-06-21 2023-12-27 Bayer Aktiengesellschaft Agrochemical formulations comprising crystalline form a of 4-[(6-chloro-3-pyridylmethyl)(2,2-difluoroethyl)amino]furan-2(5h)-one
WO2024013016A1 (en) 2022-07-11 2024-01-18 Bayer Aktiengesellschaft Herbicidal compositions
WO2024013015A1 (en) 2022-07-11 2024-01-18 Bayer Aktiengesellschaft Herbicidal compositions
WO2024068473A1 (de) 2022-09-27 2024-04-04 Bayer Aktiengesellschaft Herbizid/safener-kombinationen basierend auf safenern aus der klasse der substituierten [(1,5-diphenyl1h-1,2,4-triazol-3-yl)oxy]essigsäuren sowie deren salze
EP4295688A1 (en) 2022-09-28 2023-12-27 Bayer Aktiengesellschaft Active compound combination
WO2024068520A1 (en) 2022-09-28 2024-04-04 Bayer Aktiengesellschaft 3-(hetero)aryl-5-chlorodifluoromethyl-1,2,4-oxadiazole as fungicide
WO2024068518A1 (en) 2022-09-28 2024-04-04 Bayer Aktiengesellschaft 3-heteroaryl-5-chlorodifluoromethyl-1,2,4-oxadiazole as fungicide
WO2024068519A1 (en) 2022-09-28 2024-04-04 Bayer Aktiengesellschaft 3-(hetero)aryl-5-chlorodifluoromethyl-1,2,4-oxadiazole as fungicide
WO2024068517A1 (en) 2022-09-28 2024-04-04 Bayer Aktiengesellschaft 3-(hetero)aryl-5-chlorodifluoromethyl-1,2,4-oxadiazole as fungicide
EP4353082A1 (en) 2022-10-14 2024-04-17 Bayer Aktiengesellschaft Herbicidal compositions
WO2024104643A1 (en) 2022-11-17 2024-05-23 Bayer Aktiengesellschaft Use of isotianil for controlling plasmodiophora brassica
WO2024170472A1 (en) 2023-02-16 2024-08-22 Bayer Aktiengesellschaft Herbicidal mixtures
WO2024213752A1 (en) 2023-04-14 2024-10-17 Elanco Animal Health Gmbh Long-term prevention and/or treatment of a disease by slo-1 inhibitors

Family Cites Families (143)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH440292A (de) * 1962-01-23 1967-07-31 Ciba Geigy Verfahren zur Herstellung neuer Aminopyrazole
FR1352288A (fr) * 1963-01-22 1964-02-14 Ciba Geigy Procédé de préparation de nouveaux aminopyrazoles, entre autres du 2-butyl (secondaire)-3-amino-5-pyridyl-(3)-pyazole, de ses sels et de son dérivé n-acétylé
CA962269A (en) 1971-05-05 1975-02-04 Robert E. Grahame (Jr.) Thiazoles, and their use as insecticides
SE426011B (sv) * 1976-01-30 1982-12-06 Sixten Abrahamsson Anvendning av en helt eller partiellt deutererad acyklisk, enbasisk karboxyylayra for att skydda ett material i form av levande vexter, utsede och tre mot skadliga svampar
AU509899B2 (en) 1976-02-13 1980-05-29 E.R. Squibb & Sons, Inc. Proline derivatives and related compounds
FR2517176A1 (fr) 1981-12-01 1983-06-03 Rhone Poulenc Agrochimie Association insecticide et acaricide a base de pyrethroide
US4528291A (en) 1982-06-22 1985-07-09 Schering Corporation 2-(4'-Pyridinyl)-thiazole compounds and their use in increasing cardiac contractility
DE3520328A1 (de) 1985-06-07 1986-12-11 Bayer Ag, 5090 Leverkusen 5-amino-4-heterocyclyl-1-pyridyl-pyrazole
JPS62153273A (ja) * 1985-12-26 1987-07-08 Tokuyama Soda Co Ltd ピラゾ−ル化合物
DE3618717A1 (de) 1986-06-04 1987-12-10 Bayer Ag 5- acylamino-pyrazol-derivate
JPH07106964B2 (ja) 1987-01-14 1995-11-15 株式会社トクヤマ 摘果剤
DE3936622A1 (de) 1989-11-03 1991-05-08 Bayer Ag Halogenierte sulfonylaminocarbonyltriazolinone
US5599944A (en) 1987-03-24 1997-02-04 Bayer Aktiengesellschaft Intermediates for herbicidal sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur
JPH089541B2 (ja) 1988-03-07 1996-01-31 三井東圧化学株式会社 ピラゾール類を主成分とする脳浮腫抑制剤
US5541337A (en) 1989-04-13 1996-07-30 Bayer Aktiengesellschaft Substituted 5-alkoxy-1,2,4-triazol-3-(thi)ones
US5300480A (en) 1989-04-13 1994-04-05 Bayer Aktiengesellschaft Herbicidal sulphonylaminocarbonyltriazolinones having two substituents bonded via oxygen
US5241074A (en) 1988-05-09 1993-08-31 Bayer Aktiengesellschaft Sulphonylaminocarbonyltriazolinones
US5534486A (en) 1991-04-04 1996-07-09 Bayer Aktiengesellschaft Herbicidal sulphonylaminocarbonyl triazolinones having substituents bonded via oxygen
US5366987A (en) 1991-08-22 1994-11-22 Warner-Lambert Company Isoxazolyl-substituted alkyl amide ACAT inhibitors
TW336932B (en) 1992-12-17 1998-07-21 Pfizer Amino-substituted pyrazoles
JPH083229A (ja) 1994-06-20 1996-01-09 Sumitomo Chem Co Ltd 共重合体水溶液の製造方法
WO1997015567A1 (de) 1995-10-20 1997-05-01 Dr. Karl Thomae Gmbh 5-gliedrige heterocyclen, diese verbindungen enthaltende arzneimittel und deren verwendung sowie verfahren zu ihrer herstellung
EP0891356A1 (en) 1996-04-03 1999-01-20 Merck & Co., Inc. Inhibitors of farnesyl-protein transferase
US5854265A (en) 1996-04-03 1998-12-29 Merck & Co., Inc. Biheteroaryl inhibitors of farnesyl-protein transferase
US5854264A (en) 1996-07-24 1998-12-29 Merck & Co., Inc. Inhibitors of farnesyl-protein transferase
US6350771B1 (en) * 1996-12-24 2002-02-26 Rhone-Poulenc, Inc. Pesticidal 1-arylpyrazoles
CA2288910C (en) 1997-04-25 2003-06-24 Pfizer Inc. Pyrazolopyrimidinones for sexual dysfunction
DE19725450A1 (de) 1997-06-16 1998-12-17 Hoechst Schering Agrevo Gmbh 4-Haloalkyl-3-heterocyclylpyridine und 4-Haloalkyl-5-heterocyclylpyrimidine, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Schädlingsbekämpfungsmittel
US6271237B1 (en) 1997-12-22 2001-08-07 Dupont Pharmaceuticals Company Nitrogen containing heteromatics with ortho-substituted P1s as factor Xa inhabitors
GB9827882D0 (en) 1998-12-17 1999-02-10 Smithkline Beecham Plc Novel compounds
EA005373B1 (ru) 1999-08-12 2005-02-24 Фармация Италия С.П.А. Производные 3(5)-аминопиразола, способ их получения и их применение в качестве противоопухолевых средств
CA2382676A1 (en) 1999-11-05 2001-05-17 Warner-Lambert Company Prevention of plaque rupture by acat inhibitors
KR100724676B1 (ko) 2000-02-16 2007-06-07 이시하라 산교 가부시끼가이샤 페나실아민 유도체, 이들의 제조 방법 및 이들을 함유하는유해 생물 방제제
GB0011095D0 (en) 2000-05-08 2000-06-28 Black James Foundation astrin and cholecystokinin receptor ligands (III)
US6645990B2 (en) 2000-08-15 2003-11-11 Amgen Inc. Thiazolyl urea compounds and methods of uses
JP2002138082A (ja) * 2000-08-25 2002-05-14 Sankyo Co Ltd ４−アシルアミノピラゾール誘導体
AU2001280099A1 (en) 2000-08-25 2002-04-02 Sankyo Company Limited 4-acylaminopyrazole derivatives
US20020134012A1 (en) 2001-03-21 2002-09-26 Monsanto Technology, L.L.C. Method of controlling the release of agricultural active ingredients from treated plant seeds
JP4073786B2 (ja) 2001-04-16 2008-04-09 田辺三菱製薬株式会社 高コンダクタンス型カルシウム感受性ｋチャネル開口薬
EP1256578B1 (en) 2001-05-11 2006-01-11 Pfizer Products Inc. Thiazole derivatives and their use as cdk inhibitors
DE60204823T2 (de) 2001-07-05 2005-12-29 Pfizer Products Inc., Groton Heterocyclo-alkylsulfonyl Pyrazole als entzündungshemmende/analgetische Mittel
FR2827603B1 (fr) 2001-07-18 2003-10-17 Oreal Composes derives de diaminopyrazole substitues par un radical heteroaromatique et leur utilisation en teinture d'oxydation des fibres keratiniques
GB0123589D0 (en) 2001-10-01 2001-11-21 Syngenta Participations Ag Organic compounds
DE60222178T2 (de) 2001-12-20 2008-04-30 Sds Biotech K.K. Neue substituierte pyrazolderivate, verfahren zu deren herstellung und diese enthaltende herbizide zusammensetzung
DE60221627D1 (de) 2001-12-21 2007-09-20 Virochem Pharma Inc Thiazolderivate und ihre Verwendung zur Behandlung oder Vorbeugung von Infektionen durch Flaviviren
US6878196B2 (en) 2002-01-15 2005-04-12 Fuji Photo Film Co., Ltd. Ink, ink jet recording method and azo compound
JP2003212864A (ja) 2002-01-24 2003-07-30 Sankyo Co Ltd ５−（ｍ−シアノベンジルアミノ）チアゾール誘導体
JP2003313103A (ja) * 2002-02-20 2003-11-06 Sankyo Agro Kk ４−アシルアミノピラゾール誘導体を有効成分として含有する農薬
ATE415160T1 (de) 2002-02-25 2008-12-15 Lilly Co Eli Modulatoren von peroxisome proliferator- aktivierten rezeptoren
JP2004051628A (ja) 2002-05-28 2004-02-19 Ishihara Sangyo Kaisha Ltd ピリジン系化合物又はその塩、それらの製造方法及びそれらを含有する除草剤
US6737382B1 (en) 2002-10-23 2004-05-18 Nippon Soda Co. Ltd. Insecticidal aminothiazole derivatives
CA2504320A1 (en) 2002-10-30 2004-05-21 Vertex Pharmaceuticals Incorporated Compositions useful as inhibitors of rock and other protein kinases
US7429581B2 (en) 2002-12-23 2008-09-30 Sanofi-Aventis Deutschland Gmbh Pyrazole-derivatives as factor Xa inhibitors
JP4397615B2 (ja) 2003-03-27 2010-01-13 富士フイルム株式会社 インクジェット用インクおよびインクセット
GB0312654D0 (en) 2003-06-03 2003-07-09 Glaxo Group Ltd Therapeutically useful compounds
US7514464B2 (en) 2003-12-18 2009-04-07 Pfizer Limited Substituted arylpyrazoles
DE102004003812A1 (de) 2004-01-25 2005-08-11 Aventis Pharma Deutschland Gmbh Arylsubstituierte Heterozyklen, Verfahren ihrer Herstellung und ihre Verwendung als Arzneimittel
US7319108B2 (en) 2004-01-25 2008-01-15 Sanofi-Aventis Deutschland Gmbh Aryl-substituted heterocycles, process for their preparation and their use as medicaments
US7297168B2 (en) 2004-02-02 2007-11-20 The Procter & Gamble Company Keratin dyeing compounds, keratin dyeing compositions containing them, and use thereof
CA2560510C (en) 2004-03-18 2009-10-13 Pfizer Inc. N-(1-arylpyrazol-4yl) sulfonamides and their use as parasiticides
US20070167426A1 (en) 2004-06-02 2007-07-19 Schering Corporation Compounds for the treatment of inflammatory disorders and microbial diseases
GT200500179AA (es) * 2004-07-01 2008-10-29 Mezclas sinergistas de agentes de antranilamida para el control de plagas de invertebrados
US7705025B2 (en) 2004-08-23 2010-04-27 Eli Lilly And Company Histamine H3 receptor agents, preparation and therapeutic uses
BRPI0515571A (pt) 2004-09-23 2008-07-29 Pfizer Prod Inc agonistas de receptor de trombopoetina
MX2007005129A (es) 2004-10-27 2007-09-11 Daiichi Sankyo Co Ltd Compuesto de benceno que tiene 2 o mas sustituyentes.
CA2592118C (en) 2004-12-23 2015-11-17 Deciphera Pharmaceuticals, Llc Urea derivatives as enzyme modulators
AU2006205920B2 (en) 2005-01-14 2012-11-15 F. Hoffmann-La Roche Ag Thiazole-4-carboxamide derivatives as mGluR5 antagonists
AU2006228690A1 (en) 2005-03-31 2006-10-05 Ucb Pharma S.A. Compounds comprising an oxazole or thiazole moiety, processes for making them, and their uses
US7608592B2 (en) 2005-06-30 2009-10-27 Virobay, Inc. HCV inhibitors
TWI402034B (zh) 2005-07-28 2013-07-21 Dow Agrosciences Llc 具有被層狀液晶覆膜包覆之油球之水包油乳化劑之農用組成物
TW200800911A (en) 2005-10-20 2008-01-01 Biolipox Ab Pyrazoles useful in the treatment of inflammation
WO2007064316A1 (en) 2005-11-30 2007-06-07 Bristol-Myers Squibb Company Bicyclic heterocycles as hiv integrase inhibitors
JP2009523748A (ja) 2006-01-18 2009-06-25 シエナ ビオテク ソシエタ ペル アチオニ α７ニコチン性アセチルコリン受容体の調節物質およびそれらの治療への使用
JP2009524677A (ja) 2006-01-25 2009-07-02 シンタ ファーマシューティカルズ コーポレーション 炎症および免疫関連使用用のチアゾールおよびチアジアゾール化合物
ATE542583T1 (de) * 2006-05-22 2012-02-15 Univ Columbia Verfahren für membranlosen mikrofluidaustausch in einem h-filter und filterung der extraktionsflüssigkeitsausgangsströme
WO2008005457A2 (en) 2006-06-30 2008-01-10 Sunesis Pharmaceuticals Pyridinonyl pdk1 inhibitors
WO2008044767A1 (fr) 2006-10-13 2008-04-17 Takeda Pharmaceutical Company Limited Dérivé d'amine aromatique et utilisation de celui-ci
JP2010513519A (ja) 2006-12-22 2010-04-30 ミレニアム・ファーマシューティカルズ・インコーポレイテッド キナーゼインヒビター活性を有するある種のピラゾリン誘導体
GB0701426D0 (en) 2007-01-25 2007-03-07 Univ Sheffield Compounds and their use
JP2008280341A (ja) 2007-04-12 2008-11-20 Sumitomo Chemical Co Ltd ヒドラジド化合物およびその防除用途
WO2009011850A2 (en) 2007-07-16 2009-01-22 Abbott Laboratories Novel therapeutic compounds
WO2009055917A1 (en) 2007-11-02 2009-05-07 Methylgene Inc. Inhibitors of histone deacetylase
WO2009076454A2 (en) 2007-12-12 2009-06-18 Calcimedica, Inc. Compounds that modulate intracellular calcium
EP2071950A1 (de) * 2007-12-20 2009-06-24 Bayer CropScience AG Verfahren zur Authentizitätsprüfung von Pflanzenschutzmitteln mittels Isotopen
US8278335B2 (en) 2008-04-21 2012-10-02 Merck Sharp & Dohme Corp. Inhibitors of Janus kinases
WO2009149858A1 (de) 2008-06-13 2009-12-17 Bayer Cropscience Ag Neue heteroaromatische amide und thioamide als schädlingsbekämpfungsmittel
TW201004941A (en) 2008-07-16 2010-02-01 Wyeth Corp Alpha7 nicotinic acetylcholine receptor inhibitors
JP5681105B2 (ja) 2008-07-17 2015-03-04 バイエル・クロップサイエンス・アーゲーＢａｙｅｒ Ｃｒｏｐｓｃｉｅｎｃｅ Ａｇ 殺害虫剤として使用されるヘテロ環式化合物
JP2010030970A (ja) 2008-07-31 2010-02-12 Bayer Cropscience Ag 殺虫性ベンゼンジカルボキサミド誘導体
WO2010033360A1 (en) 2008-09-19 2010-03-25 1/3 Absolute Science, Inc. Methods of treating a botulinum toxin related condition in a subject
EP2345328A4 (en) 2008-09-19 2014-06-25 Sumitomo Chemical Co COMPOSITION FOR USE IN AGRICULTURE
JP2012503623A (ja) * 2008-09-24 2012-02-09 ビーエーエスエフ ソシエタス・ヨーロピア 無脊椎動物系害虫防除用ピラゾール化合物
NZ592603A (en) 2008-10-21 2013-02-22 Metabolex Inc Aryl gpr120 receptor agonists and uses thereof
EP2184273A1 (de) * 2008-11-05 2010-05-12 Bayer CropScience AG Halogen-substituierte Verbindungen als Pestizide
CN101747276B (zh) 2008-11-28 2011-09-07 中国中化股份有限公司 具有含氮五元杂环的醚类化合物及其应用
MX2011006332A (es) 2008-12-23 2011-06-27 Abbott Lab Compuestos antivirales.
CN102388059B (zh) 2009-02-11 2015-03-04 陶氏益农公司 杀虫组合物
US8785468B2 (en) 2009-02-13 2014-07-22 Amgen Inc. Phenylalanine amide derivatives useful for treating insulin-related diseases and conditions
UA107791C2 (en) 2009-05-05 2015-02-25 Dow Agrosciences Llc Pesticidal compositions
JP2012527414A (ja) 2009-05-19 2012-11-08 バイエル・クロップサイエンス・アーゲー 殺虫性アリールピロリン
FI20095678A0 (fi) 2009-06-16 2009-06-16 Biotie Therapies Oy Ureasubstituoituja sulfoniamidijohdannaisia
UA110324C2 (en) 2009-07-02 2015-12-25 Genentech Inc Jak inhibitory compounds based on pyrazolo pyrimidine
JP2012254939A (ja) 2009-10-07 2012-12-27 Astellas Pharma Inc オキサゾール化合物
MX2012003376A (es) 2009-10-12 2012-06-27 Bayer Cropscience Ag Amidas y tioamidas como agentes para combatir parasitos.
CN103947645B (zh) 2009-10-12 2016-07-06 拜尔农作物科学股份公司 作为杀虫剂的1-(吡啶-3-基)-吡唑和1-(嘧啶-5-基)-吡唑
US20120228235A1 (en) 2009-11-13 2012-09-13 Mehta Virendra J Method and System for Purifying Water
EP2528441A4 (en) 2010-01-25 2013-07-10 Chdi Foundation Inc CERTAIN KYNURENIN-3-MONOOXYGENASE INHIBITORS, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE THEREOF
GEP20156215B (en) 2010-02-22 2015-01-12 Syngenta Participations Ag Dihydrofuran derivatives as insecticidal compounds
NZ603156A (en) 2010-03-30 2014-10-31 Verseon Corp Multisubstituted aromatic compounds as inhibitors of thrombin
MX2012011784A (es) * 2010-04-16 2013-03-21 Bayer Ip Gmbh Nuevos compuestos heterociclicos como pesticidas.
EP2382865A1 (de) 2010-04-28 2011-11-02 Bayer CropScience AG Synergistische Wirkstoffkombinationen
BR112012028280A2 (pt) 2010-05-05 2015-09-15 Bayer Ip Gmbh derivados de tiazole como pesticidas
MX2012015292A (es) 2010-06-24 2013-05-30 Gilead Sciences Inc Pirazolo[1, 5]pirimidinas en la forma de agentes antivirales.
RU2013103422A (ru) 2010-06-28 2014-08-10 Байер Интеллектчуал Проперти Гмбх Гетероарил-замещенные пиридиновые соединения для применения в качестве пестицидов
JP2013530199A (ja) 2010-07-06 2013-07-25 ノバルティス アーゲー キナーゼ阻害剤として有用な環状エーテル化合物
WO2012007500A2 (de) * 2010-07-15 2012-01-19 Bayer Cropscience Ag Neue heterocyclische verbindungen als schädlingsbekämpfungsmittel
BR112013004920B1 (pt) 2010-08-31 2018-02-14 Dow Agrosciences Llc Moléculas úteis como pesticidas, e processos para controlar pragas
JP2012082186A (ja) 2010-09-15 2012-04-26 Bayer Cropscience Ag 殺虫性アリールピロリジン類
CN103270029B (zh) 2010-10-22 2016-01-20 拜耳知识产权有限责任公司 作为农药的杂环化合物
RU2576316C2 (ru) 2010-11-03 2016-02-27 ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи Пестицидная композиция, способ контроля вредителей, способ контроля эндопаразитов, эктопаразитов или обоих и способ усиления жизнестойкости растений
RU2571076C2 (ru) 2010-11-03 2015-12-20 ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи Пестицидная композиция
WO2012070114A1 (ja) 2010-11-24 2012-05-31 塩野義製薬株式会社 Ｎｐｙ ｙ５受容体拮抗作用を有するスルファミド誘導体
WO2012102387A1 (ja) 2011-01-27 2012-08-02 日産化学工業株式会社 ピラゾール誘導体及び有害生物防除剤
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