KR20160072154A - 살충성 화합물의 제조 방법 - Google Patents
살충성 화합물의 제조 방법 Download PDFInfo
- Publication number
- KR20160072154A KR20160072154A KR1020167012456A KR20167012456A KR20160072154A KR 20160072154 A KR20160072154 A KR 20160072154A KR 1020167012456 A KR1020167012456 A KR 1020167012456A KR 20167012456 A KR20167012456 A KR 20167012456A KR 20160072154 A KR20160072154 A KR 20160072154A
- Authority
- KR
- South Korea
- Prior art keywords
- chloro
- pyridin
- pyrazole
- pyrazol
- give
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 title claims abstract description 16
- 230000008569 process Effects 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title abstract description 8
- 230000000361 pesticidal effect Effects 0.000 title 1
- 150000003568 thioethers Chemical class 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims description 117
- -1 1- (pyridin-3-yl) -4,5-dihydro-1H-pyrazole-5-carboxylate Chemical compound 0.000 claims description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 43
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 41
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 37
- JRNVHPAWUHSFAL-UHFFFAOYSA-N 3-(3-chloropyrazol-1-yl)pyridine Chemical compound N1=C(Cl)C=CN1C1=CC=CN=C1 JRNVHPAWUHSFAL-UHFFFAOYSA-N 0.000 claims description 30
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 24
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 claims description 21
- 239000002585 base Substances 0.000 claims description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
- HBWHYODJXYJXDC-UHFFFAOYSA-N methyl 5-chloro-2-pyridin-3-ylpyrazole-3-carboxylate Chemical compound COC(=O)c1cc(Cl)nn1-c1cccnc1 HBWHYODJXYJXDC-UHFFFAOYSA-N 0.000 claims description 19
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 18
- 239000003960 organic solvent Substances 0.000 claims description 17
- WEIBBYLPUCCXKG-UHFFFAOYSA-N 3-(3-chloro-4-nitropyrazol-1-yl)pyridine Chemical compound N1=C(Cl)C([N+](=O)[O-])=CN1C1=CC=CN=C1 WEIBBYLPUCCXKG-UHFFFAOYSA-N 0.000 claims description 11
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 claims description 10
- MXERTNXQEMIYGL-UHFFFAOYSA-N 3-chloro-1-pyridin-3-ylpyrazol-4-amine Chemical compound N1=C(Cl)C(N)=CN1C1=CC=CN=C1 MXERTNXQEMIYGL-UHFFFAOYSA-N 0.000 claims description 10
- AFEVZFBTBLAWGB-UHFFFAOYSA-N 5-chloro-2-pyridin-3-ylpyrazole-3-carboxylic acid hydrochloride Chemical compound Cl.OC(=O)c1cc(Cl)nn1-c1cccnc1 AFEVZFBTBLAWGB-UHFFFAOYSA-N 0.000 claims description 10
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 10
- 150000007529 inorganic bases Chemical class 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- QJFANABRDIUIEI-UHFFFAOYSA-N pyridin-3-ylhydrazine;dihydrochloride Chemical compound Cl.Cl.NNC1=CC=CN=C1 QJFANABRDIUIEI-UHFFFAOYSA-N 0.000 claims description 9
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 8
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 8
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
- 239000003999 initiator Substances 0.000 claims description 8
- LQWHCKGJTOYJDZ-UHFFFAOYSA-N 5-chloro-2-pyridin-3-yl-3,4-dihydropyrazole-3-carbonitrile Chemical compound ClC1=NN(C(C1)C#N)c1cccnc1 LQWHCKGJTOYJDZ-UHFFFAOYSA-N 0.000 claims description 7
- OXIRKNVNDYSDCD-UHFFFAOYSA-N 5-chloro-2-pyridin-3-ylpyrazole-3-carboxylic acid Chemical compound OC(=O)C1=CC(Cl)=NN1C1=CC=CN=C1 OXIRKNVNDYSDCD-UHFFFAOYSA-N 0.000 claims description 7
- MKYDFIATDBRNHK-UHFFFAOYSA-N N-(3-chloro-1-pyridin-3-ylpyrazol-4-yl)acetamide Chemical compound CC(=O)Nc1cn(nc1Cl)-c1cccnc1 MKYDFIATDBRNHK-UHFFFAOYSA-N 0.000 claims description 7
- 239000007800 oxidant agent Substances 0.000 claims description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 6
- 239000007874 V-70 Substances 0.000 claims description 6
- WJGAPUXHSQQWQF-UHFFFAOYSA-N acetic acid;hydrochloride Chemical compound Cl.CC(O)=O WJGAPUXHSQQWQF-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 claims description 6
- 239000012320 chlorinating reagent Substances 0.000 claims description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 230000008878 coupling Effects 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 229910017604 nitric acid Inorganic materials 0.000 claims description 5
- 239000003880 polar aprotic solvent Substances 0.000 claims description 5
- FNNIAKKPBXJGNJ-UHFFFAOYSA-N pyrazolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCN1 FNNIAKKPBXJGNJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000129 anionic group Chemical group 0.000 claims description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- HTMNAAPFKKFGHH-UHFFFAOYSA-N methyl 5-chloro-2-pyridin-3-yl-3,4-dihydropyrazole-3-carboxylate Chemical compound COC(=O)C1CC(Cl)=NN1c1cccnc1 HTMNAAPFKKFGHH-UHFFFAOYSA-N 0.000 claims description 3
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 claims 7
- MOTPCOWWOZSEHC-UHFFFAOYSA-N 5-chloro-1h-pyrazole-3-carboxylic acid Chemical compound OC(=O)C=1C=C(Cl)NN=1 MOTPCOWWOZSEHC-UHFFFAOYSA-N 0.000 claims 7
- SREXTGWIUIWKRY-UHFFFAOYSA-N 5-chloro-2-pyridin-3-yl-3,4-dihydropyrazole-3-carboxylic acid Chemical compound ClC1=NN(C(C1)C(=O)O)C=1C=NC=CC=1 SREXTGWIUIWKRY-UHFFFAOYSA-N 0.000 claims 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- SUVYLXNNAGHJDN-UHFFFAOYSA-N hydron;pyridin-2-ylhydrazine;dichloride Chemical compound Cl.Cl.NNC1=CC=CC=N1 SUVYLXNNAGHJDN-UHFFFAOYSA-N 0.000 claims 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims 1
- 239000007858 starting material Substances 0.000 abstract description 9
- 150000003462 sulfoxides Chemical class 0.000 abstract description 4
- 230000000749 insecticidal effect Effects 0.000 abstract description 3
- 239000002917 insecticide Substances 0.000 abstract description 3
- 238000001311 chemical methods and process Methods 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 173
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- 235000019439 ethyl acetate Nutrition 0.000 description 58
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 41
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 239000007787 solid Substances 0.000 description 39
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000000047 product Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 24
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 23
- 239000000725 suspension Substances 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
- 241000196324 Embryophyta Species 0.000 description 19
- 239000012044 organic layer Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- 239000003480 eluent Substances 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 238000003818 flash chromatography Methods 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 14
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 11
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- KGAUNOUXSXJJRZ-UHFFFAOYSA-N 3-(3,3,3-trifluoropropylsulfanyl)propanoic acid Chemical compound OC(=O)CCSCCC(F)(F)F KGAUNOUXSXJJRZ-UHFFFAOYSA-N 0.000 description 9
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 239000002798 polar solvent Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000004809 thin layer chromatography Methods 0.000 description 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
- 239000012065 filter cake Substances 0.000 description 7
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 7
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 244000017020 Ipomoea batatas Species 0.000 description 6
- 235000002678 Ipomoea batatas Nutrition 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- 235000011089 carbon dioxide Nutrition 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 5
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical compound [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 5
- 229910000000 metal hydroxide Inorganic materials 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 4
- 241001124076 Aphididae Species 0.000 description 4
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- 238000012512 characterization method Methods 0.000 description 4
- 238000006114 decarboxylation reaction Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 235000013601 eggs Nutrition 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 150000004692 metal hydroxides Chemical class 0.000 description 4
- PBDBXAQKXCXZCJ-UHFFFAOYSA-L palladium(2+);2,2,2-trifluoroacetate Chemical compound [Pd+2].[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F PBDBXAQKXCXZCJ-UHFFFAOYSA-L 0.000 description 4
- 230000037361 pathway Effects 0.000 description 4
- 235000015497 potassium bicarbonate Nutrition 0.000 description 4
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 4
- 239000011736 potassium bicarbonate Substances 0.000 description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 4
- 238000002390 rotary evaporation Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 239000011550 stock solution Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 3
- 240000007124 Brassica oleracea Species 0.000 description 3
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 3
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 244000299507 Gossypium hirsutum Species 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- IOHOLHMGVQABTO-UHFFFAOYSA-N ethyl 5-chloro-2-pyridin-3-ylpyrazole-3-carboxylate Chemical compound CCOC(=O)c1cc(Cl)nn1-c1cccnc1 IOHOLHMGVQABTO-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 3
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- RNXRHFAQQRTRJL-UHFFFAOYSA-N methyl 3-(3,3,3-trifluoropropylsulfanyl)propanoate Chemical compound COC(=O)CCSCCC(F)(F)F RNXRHFAQQRTRJL-UHFFFAOYSA-N 0.000 description 3
- LDTLDBDUBGAEDT-UHFFFAOYSA-N methyl 3-sulfanylpropanoate Chemical compound COC(=O)CCS LDTLDBDUBGAEDT-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 3
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 3
- UDEVCZRUNOLVLU-UHFFFAOYSA-N 1-phenyloctan-1-one Chemical compound CCCCCCCC(=O)C1=CC=CC=C1 UDEVCZRUNOLVLU-UHFFFAOYSA-N 0.000 description 2
- PODZMTTVIRPETA-UHFFFAOYSA-N 3-(3,3,3-trifluoropropylsulfanyl)propanoyl chloride Chemical compound FC(F)(F)CCSCCC(Cl)=O PODZMTTVIRPETA-UHFFFAOYSA-N 0.000 description 2
- CFNLMHGOXWWOQX-UHFFFAOYSA-N 3-[(2,2-difluorocyclopropyl)methylsulfanyl]propanoic acid Chemical compound OC(=O)CCSCC1CC1(F)F CFNLMHGOXWWOQX-UHFFFAOYSA-N 0.000 description 2
- KRWUJDPGMUODRM-UHFFFAOYSA-N 5-chloro-N-ethyl-2-pyridin-3-yl-1H-pyrazol-5-amine Chemical compound ClC1(NN(C=C1)C=1C=NC=CC1)NCC KRWUJDPGMUODRM-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 241000254123 Bemisia Species 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 235000007516 Chrysanthemum Nutrition 0.000 description 2
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- 241000819999 Nymphes Species 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 244000052616 bacterial pathogen Species 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 230000000911 decarboxylating effect Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- BWSUFRYEIIZITF-UHFFFAOYSA-N ethyl 5-oxo-2-pyridin-3-ylpyrazolidine-3-carboxylate Chemical compound CCOC(=O)C1CC(=O)NN1c1cccnc1 BWSUFRYEIIZITF-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- 229910001463 metal phosphate Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- FZXISDCEHQFFHQ-UHFFFAOYSA-N n-(3-chloro-1-pyridin-3-ylpyrazol-4-yl)-n-ethylacetamide Chemical compound N1=C(Cl)C(N(C(C)=O)CC)=CN1C1=CC=CN=C1 FZXISDCEHQFFHQ-UHFFFAOYSA-N 0.000 description 2
- 230000017074 necrotic cell death Effects 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 239000003586 protic polar solvent Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000004071 soot Substances 0.000 description 2
- 238000012289 standard assay Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- YFQBFBATCINSHI-BGERDNNASA-N (2s)-2,6-diamino-1-(2-diphenoxyphosphorylpyrrolidin-1-yl)hexan-1-one Chemical compound NCCCC[C@H](N)C(=O)N1CCCC1P(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 YFQBFBATCINSHI-BGERDNNASA-N 0.000 description 1
- YMJLEPMVGQBLHL-UHFFFAOYSA-N 1h-pyrazole-5-carbonitrile Chemical compound N#CC1=CC=NN1 YMJLEPMVGQBLHL-UHFFFAOYSA-N 0.000 description 1
- OJTBJKFKQSZLFG-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CC=NN1 OJTBJKFKQSZLFG-UHFFFAOYSA-N 0.000 description 1
- TUDJNSKRXIUOAJ-UHFFFAOYSA-N 2-(bromomethyl)-1,1-difluorocyclopropane Chemical compound FC1(F)CC1CBr TUDJNSKRXIUOAJ-UHFFFAOYSA-N 0.000 description 1
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 1
- MAWGAAFDEZVGPE-UHFFFAOYSA-N 3-(5-chloro-4-methyl-3,4-dihydropyrazol-2-yl)pyridine Chemical compound ClC1=NN(CC1C)C=1C=NC=CC1 MAWGAAFDEZVGPE-UHFFFAOYSA-N 0.000 description 1
- ZBIXZFVTCIJHPH-UHFFFAOYSA-N 3-[(2,2-difluorocyclopropyl)methylsulfanyl]propanoyl chloride Chemical compound FC1(F)CC1CSCCC(Cl)=O ZBIXZFVTCIJHPH-UHFFFAOYSA-N 0.000 description 1
- DHXNZYCXMFBMHE-UHFFFAOYSA-N 3-bromopropanoic acid Chemical compound OC(=O)CCBr DHXNZYCXMFBMHE-UHFFFAOYSA-N 0.000 description 1
- SXUMSCJUXIVSFX-UHFFFAOYSA-N 3-chloro-n-ethyl-1-pyridin-3-ylpyrazol-4-amine Chemical compound N1=C(Cl)C(NCC)=CN1C1=CC=CN=C1 SXUMSCJUXIVSFX-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- XDCOYBQVEVSNNB-UHFFFAOYSA-N 4-[(7-naphthalen-2-yl-1-benzothiophen-2-yl)methylamino]butanoic acid Chemical compound OC(=O)CCCNCc1cc2cccc(-c3ccc4ccccc4c3)c2s1 XDCOYBQVEVSNNB-UHFFFAOYSA-N 0.000 description 1
- RTANHMOFHGSZQO-UHFFFAOYSA-N 4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)C#N RTANHMOFHGSZQO-UHFFFAOYSA-N 0.000 description 1
- RZCJSVRGPHXBSM-UHFFFAOYSA-N 8-chloro-[1,3]dioxolo[4,5-g]quinazoline Chemical compound C1=C2C(Cl)=NC=NC2=CC2=C1OCO2 RZCJSVRGPHXBSM-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 244000144730 Amygdalus persica Species 0.000 description 1
- 240000005528 Arctium lappa Species 0.000 description 1
- 235000003130 Arctium lappa Nutrition 0.000 description 1
- 235000008078 Arctium minus Nutrition 0.000 description 1
- 241000254127 Bemisia tabaci Species 0.000 description 1
- 241000256593 Brachycaudus schwartzi Species 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000011299 Brassica oleracea var botrytis Nutrition 0.000 description 1
- 235000017647 Brassica oleracea var italica Nutrition 0.000 description 1
- 240000003259 Brassica oleracea var. botrytis Species 0.000 description 1
- 244000178937 Brassica oleracea var. capitata Species 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 1
- 0 CC(CC1*)=NN1c1cccnc1 Chemical compound CC(CC1*)=NN1c1cccnc1 0.000 description 1
- DSGVEYCRJFCNQC-UHFFFAOYSA-N CCN(C=C1)NC1(NC1=CC=CN=C1)Cl Chemical compound CCN(C=C1)NC1(NC1=CC=CN=C1)Cl DSGVEYCRJFCNQC-UHFFFAOYSA-N 0.000 description 1
- CIUTWGBPSHYMLJ-UHFFFAOYSA-N CCNC1(C=CN(N1)C2=CC=CC=N2)Cl Chemical compound CCNC1(C=CN(N1)C2=CC=CC=N2)Cl CIUTWGBPSHYMLJ-UHFFFAOYSA-N 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 240000006432 Carica papaya Species 0.000 description 1
- 235000009467 Carica papaya Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 240000005250 Chrysanthemum indicum Species 0.000 description 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- 240000006497 Dianthus caryophyllus Species 0.000 description 1
- 235000009355 Dianthus caryophyllus Nutrition 0.000 description 1
- 240000002395 Euphorbia pulcherrima Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000007821 HATU Substances 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 241000208467 Macadamia Species 0.000 description 1
- 244000062730 Melissa officinalis Species 0.000 description 1
- 235000010654 Melissa officinalis Nutrition 0.000 description 1
- 240000005561 Musa balbisiana Species 0.000 description 1
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 1
- 241000721621 Myzus persicae Species 0.000 description 1
- 235000017879 Nasturtium officinale Nutrition 0.000 description 1
- 240000005407 Nasturtium officinale Species 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- FGZZEUJHZDWFNY-WEVVVXLNSA-N OC(/C=N/Nc1cnccc1)=O Chemical compound OC(/C=N/Nc1cnccc1)=O FGZZEUJHZDWFNY-WEVVVXLNSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 239000006002 Pepper Substances 0.000 description 1
- 235000016761 Piper aduncum Nutrition 0.000 description 1
- 240000003889 Piper guineense Species 0.000 description 1
- 235000017804 Piper guineense Nutrition 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 241000723762 Potato virus Y Species 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 244000088415 Raphanus sativus Species 0.000 description 1
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
- 241000109329 Rosa xanthina Species 0.000 description 1
- 235000004789 Rosa xanthina Nutrition 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 241000208292 Solanaceae Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- YTAHJIFKAKIKAV-XNMGPUDCSA-N [(1R)-3-morpholin-4-yl-1-phenylpropyl] N-[(3S)-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl]carbamate Chemical compound O=C1[C@H](N=C(C2=C(N1)C=CC=C2)C1=CC=CC=C1)NC(O[C@H](CCN1CCOCC1)C1=CC=CC=C1)=O YTAHJIFKAKIKAV-XNMGPUDCSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000012345 acetylating agent Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- OQIQSTLJSLGHID-WNWIJWBNSA-N aflatoxin B1 Chemical compound C=1([C@@H]2C=CO[C@@H]2OC=1C=C(C1=2)OC)C=2OC(=O)C2=C1CCC2=O OQIQSTLJSLGHID-WNWIJWBNSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- KTPZOXXVMXIMJI-UHFFFAOYSA-N ethyl 5-chloro-2-pyridin-3-yl-3,4-dihydropyrazole-3-carboxylate Chemical compound CCOC(=O)C1CC(Cl)=NN1c1cccnc1 KTPZOXXVMXIMJI-UHFFFAOYSA-N 0.000 description 1
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 235000021331 green beans Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000010422 internal standard material Substances 0.000 description 1
- BIZCJSDBWZTASZ-UHFFFAOYSA-N iodine pentoxide Inorganic materials O=I(=O)OI(=O)=O BIZCJSDBWZTASZ-UHFFFAOYSA-N 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000017448 oviposition Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 230000029553 photosynthesis Effects 0.000 description 1
- 238000010672 photosynthesis Methods 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- VNUORQWNUXXHLX-UHFFFAOYSA-N pyrazolidine-3-carboxylic acid Chemical compound OC(=O)C1CCNN1 VNUORQWNUXXHLX-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 210000005239 tubule Anatomy 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 244000000006 viral plant pathogen Species 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
- C07D213/77—Hydrazine radicals
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361892132P | 2013-10-17 | 2013-10-17 | |
| US61/892,132 | 2013-10-17 | ||
| US201462001928P | 2014-05-22 | 2014-05-22 | |
| US62/001,928 | 2014-05-22 | ||
| US201462042559P | 2014-08-27 | 2014-08-27 | |
| US62/042,559 | 2014-08-27 | ||
| PCT/US2014/061027 WO2015058028A1 (en) | 2013-10-17 | 2014-10-17 | Processes for the preparation of pesticidal compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20160072154A true KR20160072154A (ko) | 2016-06-22 |
Family
ID=52826740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020167012456A Withdrawn KR20160072154A (ko) | 2013-10-17 | 2014-10-17 | 살충성 화합물의 제조 방법 |
Country Status (9)
| Country | Link |
|---|---|
| US (6) | US9102654B2 (https=) |
| EP (1) | EP3057430A4 (https=) |
| JP (1) | JP2016539092A (https=) |
| KR (1) | KR20160072154A (https=) |
| CN (1) | CN105636441B (https=) |
| CA (1) | CA2925595A1 (https=) |
| IL (1) | IL244885A0 (https=) |
| MX (1) | MX2016004942A (https=) |
| WO (1) | WO2015058028A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20200011959A (ko) * | 2017-05-26 | 2020-02-04 | 다우 아그로사이언시즈 엘엘씨 | 피라졸 아민 반응성 결정화 |
Families Citing this family (224)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015058028A1 (en) | 2013-10-17 | 2015-04-23 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| WO2015058024A1 (en) | 2013-10-17 | 2015-04-23 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| US9174962B2 (en) * | 2013-10-17 | 2015-11-03 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| CN105636440A (zh) | 2013-10-17 | 2016-06-01 | 美国陶氏益农公司 | 制备杀虫化合物的方法 |
| JP2016536295A (ja) | 2013-10-17 | 2016-11-24 | ダウ アグロサイエンシィズ エルエルシー | 有害生物防除性化合物の製造方法 |
| US9085564B2 (en) | 2013-10-17 | 2015-07-21 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| WO2015058022A1 (en) | 2013-10-17 | 2015-04-23 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| JP2017523168A (ja) | 2014-07-31 | 2017-08-17 | ダウ アグロサイエンシィズ エルエルシー | ３−（３−クロロ−１ｈ−ピラゾール−１−イル）ピリジンの製造方法 |
| EP3174856A4 (en) | 2014-07-31 | 2018-01-10 | Dow AgroSciences LLC | Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine |
| BR112017000565A2 (pt) | 2014-07-31 | 2017-11-07 | Dow Agrosciences Llc | processo para a preparação de 3-(3-cloro-1h-pirazol-1-il)piridina |
| EP3183238A4 (en) | 2014-08-19 | 2018-01-10 | Dow AgroSciences LLC | Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine |
| BR112017004613A2 (pt) | 2014-09-12 | 2017-12-05 | Dow Agrosciences Llc | processo para a preparação de 3-(3-cloro-1h-pirazol-1-il)piridina |
| PE20181198A1 (es) | 2015-10-26 | 2018-07-23 | Bayer Cropscience Ag | Derivados de heterociclos biciclicos condensados como agentes de control de plagas |
| WO2017093180A1 (de) | 2015-12-01 | 2017-06-08 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| CN108602819A (zh) | 2015-12-03 | 2018-09-28 | 拜耳作物科学股份公司 | 作为杀虫剂的介离子卤化的3-(乙酰基)-1-[(1，3-噻唑-5-基)甲基]-1H-咪唑并[1，2-a]吡啶-4-鎓-2-醇盐衍生物和相关化合物 |
| MX2018009809A (es) | 2016-02-11 | 2018-09-10 | Bayer Cropscience Ag | 2-oximidazolilcarboxamidas sustituidas como plaguicidas. |
| US10544124B2 (en) | 2016-02-11 | 2020-01-28 | Bayer Cropscience Aktiengesellschaft | Substituted 2-(het)arylimidazolylcarboxyamides as pesticides |
| WO2017144341A1 (de) | 2016-02-23 | 2017-08-31 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| CN109152368A (zh) | 2016-03-15 | 2019-01-04 | 拜耳作物科学股份公司 | 用于防治动物害虫的取代的磺酰胺 |
| JP2019513700A (ja) | 2016-03-16 | 2019-05-30 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 殺有害生物剤及び植物保護剤としてのｎ−（シアノベンジル）−６−（シクロプロピル−カルボニルアミノ）−４−（フェニル）−ピリジン−２−カルボキサミド誘導体及び関連する化合物 |
| WO2017174414A1 (de) | 2016-04-05 | 2017-10-12 | Bayer Cropscience Aktiengesellschaft | Naphthalin-derivate als schädlingsbekämpfungsmittel |
| AU2017251155B2 (en) | 2016-04-15 | 2021-08-05 | Elanco Animal Health Gmbh | Pyrazolopyrimidine derivatives |
| EP3448845B1 (de) | 2016-04-25 | 2020-11-04 | Bayer CropScience Aktiengesellschaft | Substituierte 2-alkylimidazolyl-carboxamide als schädlingsbekämpfungsmittel |
| EP3241830A1 (de) | 2016-05-04 | 2017-11-08 | Bayer CropScience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| EP3245865A1 (en) | 2016-05-17 | 2017-11-22 | Bayer CropScience Aktiengesellschaft | Method for increasing yield in brassicaceae |
| WO2017198449A1 (en) | 2016-05-15 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in brassicaceae |
| WO2017198450A1 (en) | 2016-05-15 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in maize |
| WO2017198453A1 (en) | 2016-05-16 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in potato, tomato or alfalfa |
| WO2017198452A1 (en) | 2016-05-16 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in soybean |
| WO2017198455A2 (en) | 2016-05-17 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in beta spp. plants |
| WO2017198454A1 (en) | 2016-05-17 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in cotton |
| WO2017198451A1 (en) | 2016-05-17 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in small grain cereals such as wheat and rice |
| WO2018010163A1 (zh) * | 2016-07-15 | 2018-01-18 | 泸州东方农化有限公司 | 一种1,2,4-三唑-3-硫酮化合物的合成方法及其中间体 |
| RU2019104378A (ru) | 2016-07-19 | 2020-08-19 | Байер Кропсайенс Акциенгезельшафт | Конденсированные бициклические гетероциклические производные в качестве средств для борьбы с вредителями |
| WO2018019937A1 (en) | 2016-07-29 | 2018-02-01 | Bayer Cropscience Aktiengesellschaft | Formulation comprising a beneficial p. bilaii strain and talc for use in seed treatment |
| ES2858093T3 (es) | 2016-08-10 | 2021-09-29 | Bayer Cropscience Ag | 2-Heterociclil-imidazolil-carboxamidas sustituidas como pesticidas |
| MX2019001918A (es) | 2016-08-15 | 2019-09-06 | Bayer Cropscience Ag | Derivados del heterociclo biciclico condensado como agentes de control de plagas. |
| WO2018050825A1 (de) | 2016-09-19 | 2018-03-22 | Bayer Cropscience Aktiengesellschaft | Pyrazolo[1,5-a]pyridin- derivative und ihre verwendung als schädlingsbekämpfungsmittel |
| JP6994504B2 (ja) | 2016-10-06 | 2022-01-14 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 有害生物防除剤としての２－（ヘタ）アリール置換された縮合二環式複素環誘導体 |
| WO2018065288A1 (de) | 2016-10-07 | 2018-04-12 | Bayer Cropscience Aktiengesellschaft | 2-[2-phenyl-1-(sulfonylmethyl)vinyl]-imidazo[4,5-b]pyridin-derivate und verwandte verbindungen als schädlingsbekämpfungsmittel im pflanzenschutz |
| TW201822637A (zh) | 2016-11-07 | 2018-07-01 | 德商拜耳廠股份有限公司 | 用於控制動物害蟲的經取代磺醯胺類 |
| SI3538512T1 (sl) | 2016-11-11 | 2021-09-30 | Bayer Animal Health Gmbh | Novi antihelmintični kinolin-3-karboksamidni derivati |
| BR112019010511A2 (pt) | 2016-11-23 | 2019-09-17 | Bayer Ag | derivados de heterociclo bicíclico fundido como pesticidas |
| WO2018108791A1 (en) | 2016-12-16 | 2018-06-21 | Bayer Cropscience Aktiengesellschaft | Thiadiazole derivatives as pesticides |
| BR112019012262A2 (pt) | 2016-12-16 | 2019-12-03 | Bayer Ag | imidazopiridinas mesoiônicas para uso como inseticidas |
| WO2018125815A1 (en) | 2016-12-29 | 2018-07-05 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| CN110325036B (zh) | 2016-12-29 | 2021-10-26 | 美国陶氏益农公司 | 用于制备杀虫化合物的方法 |
| US20180186765A1 (en) | 2016-12-29 | 2018-07-05 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| UY37556A (es) | 2017-01-10 | 2018-07-31 | Bayer Ag | Derivados heterocíclicos como pesticidas |
| AR113206A1 (es) | 2017-01-10 | 2020-02-19 | Bayer Cropscience Ag | Derivados heterocíclicos como pesticidas |
| WO2018138050A1 (de) | 2017-01-26 | 2018-08-02 | Bayer Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| TW201833107A (zh) | 2017-02-06 | 2018-09-16 | 德商拜耳廠股份有限公司 | 作為殺蟲劑之經２－（雜）芳基取代的稠合雜環衍生物 |
| EP3369320A1 (de) | 2017-03-02 | 2018-09-05 | Bayer CropScience Aktiengesellschaft | Wirkstoff zur bekämpfung von wanzen |
| US20200037600A1 (en) | 2017-04-12 | 2020-02-06 | Bayer Aktiengesellschaft | Mesoionic imidazopyridines as insecticides |
| EP3612530A1 (de) | 2017-04-21 | 2020-02-26 | Bayer Aktiengesellschaft | Mesoionische imidazopyridine als insektizide |
| KR102537983B1 (ko) | 2017-04-24 | 2023-05-31 | 바이엘 악티엔게젤샤프트 | 해충 방제제로서의 축합된 비시클릭 헤테로시클릭-화합물 유도체 |
| KR102596307B1 (ko) | 2017-04-27 | 2023-10-30 | 바이엘 애니멀 헬스 게엠베하 | 새로운 비시클릭 피라졸 유도체 |
| 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 |
| KR20200003045A (ko) | 2017-05-02 | 2020-01-08 | 바이엘 악티엔게젤샤프트 | 해충 방제제로서의 2-(헤트)아릴-치환된 축합된 비시클릭 헤테로시클릭 유도체 |
| US11089783B2 (en) | 2017-05-02 | 2021-08-17 | Bayer Aktiengesellschaft | 2-(het)aryl-substituted fused heterocycle derivatives as pesticides |
| WO2018202712A1 (en) | 2017-05-03 | 2018-11-08 | Bayer Aktiengesellschaft | Trisubstitutedsilylmethylphenoxyquinolines and analogues |
| CN110650628A (zh) | 2017-05-03 | 2020-01-03 | 拜耳公司 | 三取代的甲硅烷基杂芳氧基喹啉及其类似物 |
| BR112019023037A2 (pt) | 2017-05-03 | 2020-06-02 | Bayer Aktiengesellschaft | Sisilbenzilbenzimidazóis trissubstituídos e análogos |
| WO2018202525A1 (en) | 2017-05-04 | 2018-11-08 | Bayer Cropscience Aktiengesellschaft | Phenoxyethanamine derivatives for controlling pests |
| HRP20220790T1 (hr) | 2017-05-04 | 2022-09-16 | Bayer Cropscience Aktiengesellschaft | Derivati 2-{[2-(feniloksimetil)piridin-5-il]oksi}etanamina i srodni spojevi kao pesticidi, primjerice namijenjeni zaštiti bilja |
| US11485733B2 (en) | 2017-06-30 | 2022-11-01 | Bayer Animal Health Gmbh | Azaquinoline derivatives |
| EP3284739A1 (de) | 2017-07-19 | 2018-02-21 | Bayer CropScience Aktiengesellschaft | Substituierte (het)arylverbindungen als schädlingsbekämpfungsmittel |
| KR20200036909A (ko) | 2017-08-04 | 2020-04-07 | 바이엘 애니멀 헬스 게엠베하 | 연충에 의한 감염을 치료하기 위한 퀴놀린 유도체 |
| WO2019035881A1 (en) | 2017-08-17 | 2019-02-21 | Bayer Cropscience Lp | DISPERSIBLE COMPOSITIONS IN LIQUID FERTILIZER AND ASSOCIATED METHODS |
| US10743535B2 (en) | 2017-08-18 | 2020-08-18 | H&K Solutions Llc | Insecticide for flight-capable pests |
| ES2932627T3 (es) | 2017-08-22 | 2023-01-23 | Bayer Ag | Derivados heterocíclicos como pesticidas |
| US11696913B2 (en) | 2017-09-20 | 2023-07-11 | Mitsui Chemicals Agro, Inc. | Prolonged ectoparasite-controlling agent for animal |
| USRE50663E1 (en) | 2017-10-04 | 2025-11-18 | Bayer Aktiengesellschaft | Heterocycle derivatives as pesticides |
| AU2018350611B2 (en) | 2017-10-18 | 2023-12-14 | Bayer Aktiengesellschaft | Active compound combinations having insecticidal/acaricidal properties |
| WO2019076751A1 (en) | 2017-10-18 | 2019-04-25 | Bayer Aktiengesellschaft | COMBINATIONS OF ACTIVE COMPOUNDS HAVING INSECTICIDAL / ACARICIDE PROPERTIES |
| JP7260533B2 (ja) | 2017-10-18 | 2023-04-18 | バイエル・アクチエンゲゼルシヤフト | 殺虫／殺ダニ特性を有する活性化合物の組合せ |
| SI3697217T1 (sl) | 2017-10-18 | 2021-11-30 | Bayer Aktiengesellschaft | Kombinacije aktivnih spojin, za insekticidnimi/akaricidnimi lastnostmi |
| EP3473100A1 (en) | 2017-10-18 | 2019-04-24 | Bayer Aktiengesellschaft | Active compound combinations having insecticidal/acaricidal properties |
| KR102625753B1 (ko) | 2017-10-18 | 2024-01-17 | 바이엘 악티엔게젤샤프트 | 살곤충/살진드기 특성을 갖는 활성 화합물 조합물 |
| BR112020009446A2 (pt) | 2017-11-13 | 2020-11-03 | Bayer Aktiengesellschaft | derivados de tetrazólio propila e seu uso como fungicida |
| CN111601802A (zh) | 2017-11-28 | 2020-08-28 | 拜耳股份有限公司 | 作为杀虫剂的杂环化合物 |
| 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 |
| WO2019155066A1 (en) | 2018-02-12 | 2019-08-15 | Bayer Aktiengesellschaft | Fungicidal oxadiazoles |
| US11019821B2 (en) | 2018-02-21 | 2021-06-01 | Bayer Aktiengesellschaft | Fused bicyclic heterocycle derivatives as pesticides |
| 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 |
| MX2020009320A (es) | 2018-03-08 | 2020-10-07 | Bayer Ag | Uso de compuestos heteroarilo-triazol y heteroarilo-tetrazol como plaguicidas para la proteccion de plantas. |
| US11414432B2 (en) | 2018-03-12 | 2022-08-16 | Bayer Aktiengesellschaft | Condensed bicyclic heterocyclic derivatives as pest control agents |
| US20210147371A1 (en) | 2018-04-10 | 2021-05-20 | Bayer Aktiengesellschaft | Oxadiazoline derivatives |
| FI3904350T3 (fi) | 2018-04-12 | 2023-11-15 | Bayer Ag | N-(syklopropyylimetyyli)-5-(metyylisulfonyyli)-n-{1-[1-(pyrimidin-2-yyli)-1h-1,2,4-triatsol-5-yyli]etyyli}bentsamidijohdannaisia ja vastaavia pyridiinikarboksamidijohdannaisia tuholaistorjunta-aineina |
| WO2019197615A1 (de) | 2018-04-13 | 2019-10-17 | Bayer Aktiengesellschaft | Wirkstoffkombinationen mit fungiziden, insektiziden und akariziden eigenschaften |
| WO2019197623A1 (de) | 2018-04-13 | 2019-10-17 | Bayer Aktiengesellschaft | Wirkstoffkombinationen mit insektiziden, nematiziden und akariziden eigenschaften |
| UY38184A (es) | 2018-04-17 | 2019-10-31 | Bayer Ag | Compuestos heteroarilo-triazol y heteroarilo-tetrazol novedosos como plaguicidas |
| WO2019202077A1 (en) | 2018-04-20 | 2019-10-24 | Bayer Aktiengesellschaft | Heteroaryl-triazole and heteroaryl-tetrazole compounds as pesticides |
| WO2019201921A1 (de) | 2018-04-20 | 2019-10-24 | Bayer Aktiengesellschaft | Heterocyclen-derivate als schädlingsbekämpfungsmittel |
| KR102709679B1 (ko) | 2018-04-25 | 2024-09-26 | 바이엘 악티엔게젤샤프트 | 살충제로서의 신규 헤테로아릴-트리아졸 및 헤테로아릴-테트라졸 화합물 |
| CN108658942B (zh) * | 2018-04-28 | 2020-06-30 | 中南民族大学 | 一种基于氧代氮杂环丁烷吡唑羧酸酯化合物及其微波水热法合成方法和应用 |
| US11572357B2 (en) | 2018-05-09 | 2023-02-07 | Bayer Animal Health Gmbh | Quinoline derivatives |
| WO2019224143A1 (de) | 2018-05-24 | 2019-11-28 | Bayer Aktiengesellschaft | Wirkstoffkombinationen mit insektiziden, nematiziden und akariziden eigenschaften |
| WO2020005678A1 (en) | 2018-06-25 | 2020-01-02 | Bayer Cropscience Lp | Seed treatment method |
| EP3586630A1 (en) | 2018-06-28 | 2020-01-01 | Bayer AG | Active compound combinations having insecticidal/acaricidal properties |
| AU2019297402B2 (en) | 2018-07-05 | 2024-05-02 | Bayer Aktiengesellschaft | Substituted thiophenecarboxamides and analogues as antibacterials agents |
| WO2020020813A1 (en) | 2018-07-25 | 2020-01-30 | Bayer Aktiengesellschaft | Fungicidal active compound combinations |
| WO2020020816A1 (en) | 2018-07-26 | 2020-01-30 | Bayer Aktiengesellschaft | Novel triazole derivatives |
| 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 |
| EP3852532A1 (en) | 2018-09-17 | 2021-07-28 | Bayer Aktiengesellschaft | Use of the fungicide isoflucypram for controlling claviceps purpurea and reducing sclerotia in cereals |
| 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 |
| JP2022512712A (ja) | 2018-10-18 | 2022-02-07 | バイエル・アクチエンゲゼルシヤフト | ヘテロアリールアミノキノリン類及び類似体 |
| KR20210081370A (ko) | 2018-10-18 | 2021-07-01 | 바이엘 악티엔게젤샤프트 | 피리딜페닐아미노퀴놀린 및 유사체 |
| 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 |
| AR117169A1 (es) | 2018-11-28 | 2021-07-14 | Bayer Ag | (tio)amidas de piridazina como compuestos fungicidas |
| ES2942215T3 (es) | 2018-12-07 | 2023-05-30 | Bayer Ag | Composiciones herbicidas |
| HRP20230284T1 (hr) | 2018-12-07 | 2023-05-12 | Bayer Aktiengesellschaft | Herbicidne kombinacije |
| 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 |
| PY19106036A (es) | 2018-12-20 | 2021-07-06 | Bayer Ag | Compuestos de heterociclil piridazina como fungicidas |
| EP3669652A1 (en) | 2018-12-21 | 2020-06-24 | Bayer AG | Active compound combination |
| PY19106549A (es) | 2018-12-21 | 2021-07-13 | Bayer Ag | 1,3,4-oxadiazoles y derivados de éstos como nuevos agentes fungicidas |
| EP3679789A1 (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 |
| EP3679790A1 (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 |
| 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 |
| PY2012000A (es) | 2019-02-26 | 2023-07-25 | Bayer Ag | Derivados de heterociclos bicíclicos fusionados como pesticidas |
| PY2011993A (es) | 2019-02-26 | 2021-07-05 | Bayer Ag | Derivados heterocíclos bicíclicos condensados como plaguicida |
| 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 |
| MX2021013613A (es) | 2019-05-08 | 2021-12-10 | Bayer Ag | Combinacion de compuestos activos. |
| BR112021022308A2 (pt) | 2019-05-08 | 2021-12-28 | Bayer Ag | Formulações de ulv de alto espalhamento para inseticidas |
| WO2020231751A1 (en) | 2019-05-10 | 2020-11-19 | 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 |
| WO2020254489A1 (en) | 2019-06-21 | 2020-12-24 | Bayer Aktiengesellschaft | Benzylphenyl hydroxyisoxazolines and analogues as new antifungal agents |
| BR112021025264A2 (pt) | 2019-06-21 | 2022-01-25 | Bayer Ag | Fenoxifenil hidróxi-isoxazolinas e análogos como novos agentes antifúngicos |
| EP3986891A1 (en) | 2019-06-21 | 2022-04-27 | Bayer Aktiengesellschaft | Hydroxyisoxazolines and derivatives thereof |
| BR112021025300A2 (pt) | 2019-06-21 | 2022-02-01 | Bayer Ag | Oxadiazóis fungicidas |
| WO2020254492A1 (en) | 2019-06-21 | 2020-12-24 | Bayer Aktiengesellschaft | Hydroxyisoxazolines and derivatives thereof |
| EP3986877A1 (en) | 2019-06-21 | 2022-04-27 | Bayer Aktiengesellschaft | Hydroxyisoxazolines and derivatives thereof |
| EP3986892A1 (en) | 2019-06-21 | 2022-04-27 | Bayer Aktiengesellschaft | Hydroxyisoxazolines and use thereof as fungicides |
| BR112021025317A2 (pt) | 2019-06-21 | 2022-03-15 | Bayer Ag | Tienilhidroxiisoxazolinas e derivados das mesmas |
| WO2020263812A1 (en) | 2019-06-24 | 2020-12-30 | Auburn University | A bacillus strain and methods of its use for plant growth promotion |
| 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 |
| CA3145592A1 (en) | 2019-07-03 | 2021-01-07 | Bayer Aktiengesellschaft | Substituted thiophene carboxamides and derivatives thereof as microbicides |
| PT3993626T (pt) | 2019-07-04 | 2025-02-10 | Bayer Ag | Composições herbicidas |
| TWI865563B (zh) | 2019-07-30 | 2024-12-11 | 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 |
| WO2021058659A1 (en) | 2019-09-26 | 2021-04-01 | Bayer Aktiengesellschaft | Rnai-mediated pest control |
| 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 |
| US20220380318A1 (en) | 2019-11-07 | 2022-12-01 | Bayer Aktiengesellschaft | Substituted sulfonyl amides for controlling animal pests |
| WO2021097162A1 (en) | 2019-11-13 | 2021-05-20 | Bayer Cropscience Lp | Beneficial combinations with paenibacillus |
| CN118496197A (zh) | 2019-12-20 | 2024-08-16 | 拜耳公司 | 取代的噻吩甲酰胺、噻吩甲酸及其衍生物 |
| MA58019B1 (fr) | 2019-12-20 | 2024-10-31 | Bayer Aktiengesellschaft | Thienyloxazolones et analogues |
| EP3845304A1 (en) | 2019-12-30 | 2021-07-07 | Bayer AG | Capsule suspension concentrates based on polyisocyanates and biodegradable amine based cross-linker |
| PY2112437A (es) | 2020-02-18 | 2022-08-16 | Bayer Ag | Nuevos compuestos de heteroaril-triazol como pesticidas |
| 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 |
| HUE069397T2 (hu) | 2020-04-16 | 2025-03-28 | Bayer Ag | Hatóanyag-kombinációk és azokat tartalmazó fungicid készítmények |
| WO2021209363A1 (en) | 2020-04-16 | 2021-10-21 | Bayer Aktiengesellschaft | Active compound combinations and fungicide compositions comprising those |
| WO2021209490A1 (en) | 2020-04-16 | 2021-10-21 | Bayer Aktiengesellschaft | Cyclaminephenylaminoquinolines as fungicides |
| WO2021209366A1 (en) | 2020-04-16 | 2021-10-21 | Bayer Aktiengesellschaft | Active compound combinations and fungicide compositions comprising those |
| CN115551352B (zh) | 2020-04-16 | 2024-11-08 | 拜耳公司 | 活性化合物组合以及包含它们的杀真菌剂组合物 |
| AR121829A1 (es) | 2020-04-16 | 2022-07-13 | Bayer Ag | Combinaciones de compuestos activos y composiciones fungicidas que los comprenden |
| EP4146628A1 (en) | 2020-05-06 | 2023-03-15 | Bayer Aktiengesellschaft | Pyridine (thio)amides as fungicidal compounds |
| WO2021228734A1 (en) | 2020-05-12 | 2021-11-18 | Bayer Aktiengesellschaft | Triazine and pyrimidine (thio)amides as fungicidal compounds |
| EP4153566A1 (en) | 2020-05-19 | 2023-03-29 | Bayer CropScience Aktiengesellschaft | Azabicyclic(thio)amides as fungicidal compounds |
| US12565489B2 (en) | 2020-06-04 | 2026-03-03 | Bayer Aktiengesellschaft | Heterocyclyl pyrimidines and triazines as novel fungicides |
| CA3186659A1 (en) | 2020-06-10 | 2021-12-16 | Bayer Aktiengesellschaft | Azabicyclyl-substituted heterocycles as fungicides |
| CN116157017A (zh) | 2020-06-18 | 2023-05-23 | 拜耳公司 | 作为杀菌剂用于作物保护的3-(哒嗪-4-基)-5,6-二氢-4h-1,2,4-噁二嗪衍生物 |
| 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 |
| WO2021255091A1 (en) | 2020-06-19 | 2021-12-23 | Bayer Aktiengesellschaft | 1,3,4-oxadiazoles and their derivatives as fungicides |
| 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. |
| WO2021255089A1 (en) | 2020-06-19 | 2021-12-23 | Bayer Aktiengesellschaft | 1,3,4-oxadiazole pyrimidines and 1,3,4-oxadiazole pyridines as fungicides |
| WO2021260017A1 (en) | 2020-06-26 | 2021-12-30 | Bayer Aktiengesellschaft | Aqueous capsule suspension concentrates comprising biodegradable ester groups |
| WO2022058327A1 (en) | 2020-09-15 | 2022-03-24 | Bayer Aktiengesellschaft | Substituted ureas and derivatives as new antifungal agents |
| EP3915371A1 (en) | 2020-11-04 | 2021-12-01 | Bayer AG | Active compound combinations and fungicide compositions comprising those |
| EP3994994A1 (en) | 2020-11-08 | 2022-05-11 | Bayer Aktiengesellschaft | Low drift, rainfastness, high spreading, high uptake 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 |
| 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 |
| EP3994992A1 (en) | 2020-11-08 | 2022-05-11 | Bayer AG | Low drift, rainfastness, 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 |
| EP3994995A1 (en) | 2020-11-08 | 2022-05-11 | Bayer Aktiengesellschaft | Low drift, rainfastness, high spreading, high uptake and ulv tank mix adjuvant formulation |
| EP3994988A1 (en) | 2020-11-08 | 2022-05-11 | Bayer AG | Agrochemical composition with improved drift, spreading and rainfastness properties |
| EP3994987A1 (en) | 2020-11-08 | 2022-05-11 | Bayer AG | Agrochemical composition with improved drift and uptake properties |
| EP3994985A1 (en) | 2020-11-08 | 2022-05-11 | Bayer Aktiengesellschaft | Agrochemical composition with improved drift 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 |
| WO2022129188A1 (en) | 2020-12-18 | 2022-06-23 | Bayer Aktiengesellschaft | 1,2,4-oxadiazol-3-yl pyrimidines as fungicides |
| WO2022129196A1 (en) | 2020-12-18 | 2022-06-23 | Bayer Aktiengesellschaft | Heterobicycle substituted 1,2,4-oxadiazoles as fungicides |
| WO2022152728A1 (de) | 2021-01-15 | 2022-07-21 | Bayer Aktiengesellschaft | Herbizide zusammensetzungen |
| EP4337017A1 (de) | 2021-05-10 | 2024-03-20 | 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 |
| EP4148052A1 (en) | 2021-09-09 | 2023-03-15 | Bayer Animal Health GmbH | New quinoline derivatives |
| 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 |
| CN119233755A (zh) | 2022-05-07 | 2024-12-31 | 拜耳公司 | 用于低、中等和高喷雾量施用的低漂移水性液体制剂 |
| WO2024013016A1 (en) | 2022-07-11 | 2024-01-18 | Bayer Aktiengesellschaft | Herbicidal compositions |
| WO2024013015A1 (en) | 2022-07-11 | 2024-01-18 | Bayer Aktiengesellschaft | Herbicidal compositions |
| AU2023353668A1 (en) | 2022-09-27 | 2025-04-10 | Bayer Aktiengesellschaft | Herbicide/safener combination based on safeners from the class of substituted [(1,5-diphenyl-1h-1,2,4-triazol-3-yl)oxy]acetic acids and their salts |
| EP4353082A1 (en) | 2022-10-14 | 2024-04-17 | Bayer Aktiengesellschaft | Herbicidal compositions |
| EP4665151A1 (en) | 2023-02-16 | 2025-12-24 | 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 |
| WO2025031668A1 (en) | 2023-08-09 | 2025-02-13 | Bayer Aktiengesellschaft | Azaheterobiaryl-substituted 4,5-dihydro-1h-2,4,5-oxadiazines as novel fungicides |
| WO2025040301A1 (de) | 2023-08-21 | 2025-02-27 | Bayer Aktiengesellschaft | Herbizid/safener-kombinationen basierend auf safenern aus der klasse der substituierten [(1,5-diphenyl-1h-1,2,4-triazol-3-yl)oxy]essigsäuren und herbiziden aus der klasse der substituierten cyclischen dione sowie deren salze |
| CN121908950A (zh) | 2023-08-21 | 2026-04-21 | 拜耳公司 | 基于取代的[(1,5-二苯基-1h-1,2,4-三唑-3-基)氧基]乙酸类的安全剂与取代的环二酮类及其盐的除草剂的除草剂/安全剂结合物 |
| WO2025078128A1 (en) | 2023-10-11 | 2025-04-17 | Bayer Aktiengesellschaft | Pyridazin-3-one-4-yloxadiazines as novel fungicides |
| WO2025108865A1 (de) | 2023-11-23 | 2025-05-30 | Bayer Aktiengesellschaft | Herbizide zusammensetzungen |
| WO2025132148A1 (en) | 2023-12-21 | 2025-06-26 | Bayer Aktiengesellschaft | Adjuvant compositions for agrochemical applications |
| WO2025168620A1 (en) | 2024-02-07 | 2025-08-14 | Bayer Aktiengesellschaft | Heteroaryl-substituted 4,5-dihydro-1h-2,4,5-oxadiazines as novel fungicides |
| WO2026078157A2 (en) | 2024-10-10 | 2026-04-16 | Elanco Animal Health Gmbh | Slo-1 modulators for prevention and/or treatment of a disease |
| CN120904152B (zh) * | 2025-09-25 | 2026-02-27 | 西安思科赛实业有限公司 | 一种卤代吡啶基吡唑烷羧酸酯的合成工艺 |
Family Cites Families (174)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3597341A (en) | 1968-09-11 | 1971-08-03 | Exxon Research Engineering Co | Selective addition of thiols to allylic isocyanates and isothiocyanates |
| CA962269A (en) | 1971-05-05 | 1975-02-04 | Uniroyal Ltd. | Thiazoles, and their use as insecticides |
| US4556671A (en) | 1979-07-13 | 1985-12-03 | Burroughs Wellcome Co. | Pharmaceutical formulations |
| US4407803A (en) | 1981-08-17 | 1983-10-04 | Abbott Laboratories | Antiinflammatory 1-(quinolinyl)-2-pyrazoline derivatives |
| 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 |
| US4824953A (en) | 1983-11-15 | 1989-04-25 | Riker Laboratories, Inc. | Multi-step process for producing 5-hydroxy-N-(6-oxo-piperidyl-methyl)-2-(2,2,2-trifluoro-ethoxy)-benzamide and derivatives |
| ATE49198T1 (de) | 1984-05-12 | 1990-01-15 | Fisons Plc | Antiinflammatorische 1,n-diarylpyrazol-3-amine, deren zusammensetzungen und verfahren zu deren herstellung. |
| IT1183181B (it) * | 1985-02-07 | 1987-10-05 | Corvi Camillo Spa | Derivati del 3-metil-imidazo(4,5-c)pirazolo con attivita' terapeutica e procedimento per la loropreparazione |
| DE3520328A1 (de) | 1985-06-07 | 1986-12-11 | Bayer Ag, 5090 Leverkusen | 5-amino-4-heterocyclyl-1-pyridyl-pyrazole |
| GB8625897D0 (en) | 1986-10-29 | 1986-12-03 | Ici Plc | Insecticidal thioethers derivatives |
| JPS62153273A (ja) | 1985-12-26 | 1987-07-08 | Tokuyama Soda Co Ltd | ピラゾ−ル化合物 |
| DE3600950A1 (de) | 1986-01-15 | 1987-07-16 | Bayer Ag | 5-acylamido-1-aryl-pyrazole |
| JPS62153273U (https=) | 1986-03-19 | 1987-09-29 | ||
| 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 |
| US5599944A (en) | 1987-03-24 | 1997-02-04 | Bayer Aktiengesellschaft | Intermediates for herbicidal sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur |
| DE3936622A1 (de) | 1989-11-03 | 1991-05-08 | Bayer Ag | Halogenierte sulfonylaminocarbonyltriazolinone |
| JPS63174905U (https=) | 1987-04-23 | 1988-11-14 | ||
| 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 |
| US5300480A (en) | 1989-04-13 | 1994-04-05 | Bayer Aktiengesellschaft | Herbicidal sulphonylaminocarbonyltriazolinones having two substituents bonded via oxygen |
| US5541337A (en) | 1989-04-13 | 1996-07-30 | Bayer Aktiengesellschaft | Substituted 5-alkoxy-1,2,4-triazol-3-(thi)ones |
| US5241074A (en) | 1988-05-09 | 1993-08-31 | Bayer Aktiengesellschaft | Sulphonylaminocarbonyltriazolinones |
| US5220028A (en) | 1988-10-27 | 1993-06-15 | Nissan Chemical Industries, Ltd. | Halogeno-4-methylpyrazoles |
| 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 |
| JPH11513382A (ja) | 1995-10-20 | 1999-11-16 | ドクトル カルル トーマエ ゲゼルシャフト ミット ベシュレンクテル ハフツング | ５員複素環化合物、これらの化合物を含む医薬品、それらの使用及びそれらの調製方法 |
| US5854265A (en) | 1996-04-03 | 1998-12-29 | Merck & Co., Inc. | Biheteroaryl inhibitors of farnesyl-protein transferase |
| CA2249665A1 (en) | 1996-04-03 | 1997-10-09 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| TW430660B (en) * | 1996-05-30 | 2001-04-21 | Mochida Pharm Co Ltd | Novel benzindole derivatives for neuron cell protection, processes for production, and the pharmaceutical compounds containing them |
| US5854264A (en) | 1996-07-24 | 1998-12-29 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| US6723719B1 (en) | 1997-04-25 | 2004-04-20 | Pfizer Inc | Pyrazolopyrimidinones which inhibit type 5 cyclic guanosine 3′,5′—monophosphate phosphodiesterase (cGMP PDE5) for the treatment of 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 |
| WO1999062885A1 (en) * | 1998-06-05 | 1999-12-09 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substituted 1-(4-aminophenyl)pyrazoles and their use as anti-inflammatory agents |
| GB9827882D0 (en) | 1998-12-17 | 1999-02-10 | Smithkline Beecham Plc | Novel compounds |
| FR2789076B1 (fr) | 1999-02-02 | 2001-03-02 | Synthelabo | Derives de alpha-azacyclomethyl quinoleine, leur preparation et leur application en therapeutique |
| FR2789387B1 (fr) | 1999-02-04 | 2001-09-14 | Aventis Cropscience Sa | Nouveau procede de preparation d'intermediaires pesticides |
| WO2001012189A1 (en) | 1999-08-12 | 2001-02-22 | Pharmacia Italia S.P.A. | 3(5)-amino-pyrazole derivatives, process for their preparation and their use as antitumor agents |
| HUP0203160A3 (en) | 1999-11-05 | 2006-02-28 | Warner Lambert Co | Prevention of plaque rupture by acat inhibitors |
| CN1307161A (zh) * | 2000-01-26 | 2001-08-08 | 惠阳市沥林国翔瓷砖工艺加工厂 | 网模石子贴及其制造方法 |
| EP1256569B1 (en) | 2000-02-16 | 2010-07-07 | Ishihara Sangyo Kaisha, Ltd. | Phenacylamine derivatives, production thereof and pest controllers containing the derivatives |
| 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 |
| WO2002023986A1 (en) | 2000-08-25 | 2002-03-28 | Sankyo Company, Limited | 4-acylaminopyrazole derivatives |
| KR20030030029A (ko) | 2000-09-22 | 2003-04-16 | 니혼노야쿠가부시키가이샤 | Ｎ-(4-피라졸릴)아미드 유도체 및 농원예용 약제 그리고그 사용방법 |
| 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 |
| CZ20032829A3 (cs) | 2001-04-16 | 2005-03-16 | Tanabe Seiyaku Co., Ltd. | Heterocyklické sloučeniny |
| EP1256578B1 (en) | 2001-05-11 | 2006-01-11 | Pfizer Products Inc. | Thiazole derivatives and their use as cdk inhibitors |
| ES2241964T3 (es) | 2001-07-05 | 2005-11-01 | Pfizer Products Inc. | Heterocicloalquilsulfufonilpirazoles como agentes antiinflamatorios/abnalgesicos. |
| 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 |
| TWI356822B (en) * | 2001-08-13 | 2012-01-21 | Du Pont | Novel substituted dihydro 3-halo-1h-pyrazole-5-car |
| GB0123589D0 (en) | 2001-10-01 | 2001-11-21 | Syngenta Participations Ag | Organic compounds |
| CN100532363C (zh) | 2001-12-20 | 2009-08-26 | 株式会社Sds生技 | 取代的吡唑衍生物及其制备方法以及含该衍生物的除草剂组合物 |
| 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 |
| US7259175B2 (en) | 2002-02-25 | 2007-08-21 | Eli Lilly And Company | Peroxisome proliferator activated receptor modulators |
| 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 |
| AU2003254053A1 (en) | 2002-07-23 | 2004-02-09 | Smithkline Beecham Corporation | Pyrazolopyrimidines as protein kinase inhibitors |
| US6737382B1 (en) | 2002-10-23 | 2004-05-18 | Nippon Soda Co. Ltd. | Insecticidal aminothiazole derivatives |
| AR043057A1 (es) | 2002-10-30 | 2005-07-13 | Vertex Pharma | Compuestos derivados de piridintiazoles como inhibidores de la quinasa rock y otras proteinas quinasa |
| CA2508412C (en) | 2002-12-03 | 2011-07-26 | Bayer Cropscience S.A. | Pesticidal 5-(acylamino) pyrazole derivatives |
| 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 |
| EP1671937A4 (en) * | 2003-09-19 | 2007-08-08 | Ube Industries | METHOD FOR PRODUCING A NITRILE COMPOUND, CARBOXYLIC COMPOUND OR CARBOXYLATE COMPOUND |
| CN100432038C (zh) * | 2003-09-19 | 2008-11-12 | 宇部兴产株式会社 | 腈化合物、羧酸化合物或羧酸酯化合物的制备方法 |
| US7514464B2 (en) | 2003-12-18 | 2009-04-07 | Pfizer Limited | Substituted arylpyrazoles |
| US7319108B2 (en) | 2004-01-25 | 2008-01-15 | Sanofi-Aventis Deutschland Gmbh | Aryl-substituted heterocycles, process for their preparation and their use as medicaments |
| DE102004003812A1 (de) | 2004-01-25 | 2005-08-11 | Aventis Pharma Deutschland Gmbh | Arylsubstituierte Heterozyklen, Verfahren ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US7297168B2 (en) | 2004-02-02 | 2007-11-20 | The Procter & Gamble Company | Keratin dyeing compounds, keratin dyeing compositions containing them, and use thereof |
| AU2005223483B2 (en) | 2004-03-18 | 2009-04-23 | Zoetis Llc | N-(1-arylpyrazol-4l)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 | |
| CN101006082B (zh) | 2004-08-23 | 2010-09-29 | 伊莱利利公司 | 组胺h3受体药剂、制备方法和治疗用途 |
| MX2007003377A (es) | 2004-09-23 | 2007-05-10 | Pfizer Prod Inc | Agonistas del receptor de trombopoyetina. |
| TW200619191A (en) | 2004-10-27 | 2006-06-16 | Sankyo Co | Phenyl compounds with more than 2 substitutes |
| CA2592118C (en) | 2004-12-23 | 2015-11-17 | Deciphera Pharmaceuticals, Llc | Urea derivatives as enzyme modulators |
| BRPI0606644A2 (pt) | 2005-01-14 | 2009-07-14 | Hoffmann La Roche | derivados de 4-carboxamida tiazola |
| CA2602336A1 (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 |
| CN101228134A (zh) | 2005-06-15 | 2008-07-23 | 辉瑞有限公司 | 用作杀寄生虫剂的取代芳基吡唑 |
| US7608592B2 (en) | 2005-06-30 | 2009-10-27 | Virobay, Inc. | HCV inhibitors |
| KR100654328B1 (ko) * | 2005-08-26 | 2006-12-08 | 한국과학기술연구원 | 피페라지닐알킬피라졸계 ｔ-타입 칼슘 채널 억제 화합물 및이의 제조방법 |
| WO2007098826A2 (en) | 2006-01-18 | 2007-09-07 | Siena Biotech S.P.A. | Modulators of alpha7 nicotinic acetylcholine receptors and therapeutic uses thereof |
| US8455658B2 (en) | 2006-01-25 | 2013-06-04 | Synta Pharmaceuticals Corp. | Thiazole and thiadiazole compounds for inflammation and immune-related uses |
| EP2038272B8 (en) | 2006-06-30 | 2013-10-23 | Sunesis Pharmaceuticals, Inc. | Pyridinonyl pdk1 inhibitors |
| WO2008044767A1 (en) | 2006-10-13 | 2008-04-17 | Takeda Pharmaceutical Company Limited | Aromatic amine derivative and use thereof |
| JO2754B1 (en) * | 2006-12-21 | 2014-03-15 | استرازينكا ايه بي | Amylendazoleil derivatives for the treatment of glucocorticoid-mediated disorders |
| US7795249B2 (en) | 2006-12-22 | 2010-09-14 | Millennium Pharmaceuticals, Inc. | Certain pyrazoline derivatives with kinase inhibitory activity |
| GB0701426D0 (en) | 2007-01-25 | 2007-03-07 | Univ Sheffield | Compounds and their use |
| WO2009011850A2 (en) | 2007-07-16 | 2009-01-22 | Abbott Laboratories | Novel therapeutic compounds |
| EP2173728A2 (en) | 2007-07-17 | 2010-04-14 | Amgen Inc. | Heterocyclic modulators of pkb |
| ES2423181T3 (es) | 2007-07-17 | 2013-09-18 | F. Hoffmann-La Roche Ag | Inhibidores de la 11ß-hidroxiesteroide-deshidrogenasa |
| WO2009015193A1 (en) | 2007-07-23 | 2009-01-29 | Replidyne, Inc. | Antibacterial sulfone and sulfoxide substituted heterocyclic urea compounds |
| CN101918389A (zh) | 2007-11-02 | 2010-12-15 | 梅特希尔基因公司 | 组蛋白脱乙酰酶抑制剂 |
| US8389567B2 (en) | 2007-12-12 | 2013-03-05 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| NZ587143A (en) * | 2008-02-12 | 2011-07-29 | Dow Agrosciences Llc | Pesticidal compositions |
| EP2246377B1 (en) | 2008-02-15 | 2014-08-27 | Asahi Kasei E-materials Corporation | Resin composition |
| EP2278969B1 (en) | 2008-04-21 | 2013-02-13 | Merck Sharp & Dohme Corp. | Inhibitors of Janus kinases |
| MX2010013705A (es) | 2008-06-13 | 2011-02-25 | Bayer Cropscience Ag | Nuevas amidas y tioamidas heteroaromaticas como plaguicidas. |
| TW201004941A (en) | 2008-07-16 | 2010-02-01 | Wyeth Corp | Alpha7 nicotinic acetylcholine receptor inhibitors |
| EP2583556B1 (de) | 2008-07-17 | 2016-01-20 | Bayer CropScience AG | Heterocyclische Verbindungen als Schädlingsbekämpfungsmittel |
| 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 |
| CA2737437A1 (en) | 2008-09-19 | 2010-03-25 | Absolute Science, Inc. | Methods of treating a botulinum toxin related condition in a subject |
| WO2010032874A1 (ja) | 2008-09-19 | 2010-03-25 | 住友化学株式会社 | 農業用組成物 |
| GB0817617D0 (en) | 2008-09-25 | 2008-11-05 | Ricardo Uk Ltd | Bearing for wind turbine |
| EA022417B1 (ru) | 2008-10-21 | 2015-12-30 | Саймабэй Терапевтикс, Инк. | Арильные агонисты рецептора gpr120 и их применение |
| 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 |
| SG172352A1 (en) | 2008-12-23 | 2011-07-28 | Abbott Lab | Anti-viral compounds |
| AU2010213749B2 (en) | 2009-02-11 | 2015-01-22 | Dow Agrosciences Llc | Pesticidal compositions |
| US8785468B2 (en) | 2009-02-13 | 2014-07-22 | Amgen Inc. | Phenylalanine amide derivatives useful for treating insulin-related diseases and conditions |
| GB0904100D0 (en) | 2009-03-10 | 2009-04-22 | Bradford Pharma Ltd | Use of rosuvastatin lactols as medicaments |
| UA107791C2 (en) | 2009-05-05 | 2015-02-25 | Dow Agrosciences Llc | Pesticidal compositions |
| ES2536278T3 (es) | 2009-05-19 | 2015-05-22 | Bayer Intellectual Property Gmbh | Arilpirrolinas insecticidas |
| 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 |
| KR20120046765A (ko) | 2009-08-10 | 2012-05-10 | 스미또모 가가꾸 가부시끼가이샤 | (플루오로알킬티오)아세트산에스테르의 제조 방법 |
| JP2012254939A (ja) | 2009-10-07 | 2012-12-27 | Astellas Pharma Inc | オキサゾール化合物 |
| EP2488510B1 (de) | 2009-10-12 | 2017-03-29 | Bayer Intellectual Property GmbH | Amide und Thioamide als Schädlingsbekämpfungsmittel |
| BR112012006956A2 (pt) | 2009-10-12 | 2015-09-15 | Bayer Cropscience Ag | 1- (pirida-3-il) -pirazóisol e 1- (pirimida-5-il) - pirazóisol como pesticidas |
| CA2787365A1 (en) | 2010-01-25 | 2011-07-28 | Chdi Foundation, Inc. | Certain kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| EA201201171A1 (ru) | 2010-02-22 | 2013-03-29 | Зингента Партисипейшнс Аг | Дигидрофурановые производные в качестве инсектицидных соединений |
| CN102918034B (zh) | 2010-03-30 | 2015-06-03 | 维颂公司 | 多取代芳族化合物作为凝血酶的抑制剂 |
| EP2558458B1 (de) | 2010-04-16 | 2017-09-06 | Bayer Intellectual Property GmbH | Neue heterocyclische verbindungen als schädlingsbekämpfungsmittel |
| EP2382865A1 (de) | 2010-04-28 | 2011-11-02 | Bayer CropScience AG | Synergistische Wirkstoffkombinationen |
| CN102971315B (zh) | 2010-05-05 | 2015-07-22 | 拜耳知识产权有限责任公司 | 作为害虫防治剂的噻唑衍生物 |
| PT3012258T (pt) | 2010-06-24 | 2018-12-14 | Gilead Sciences Inc | Composição farmacêutica compreendendo um derivado de pirazolo[1,5-a]pirimidina como agente antiviral |
| CA2803695A1 (en) | 2010-06-28 | 2012-01-05 | Bayer Intellectual Property Gmbh | Heteroaryl-substituted pyridine compounds for use as pesticides |
| US20130109682A1 (en) | 2010-07-06 | 2013-05-02 | Novartis Ag | Cyclic ether compounds useful as kinase inhibitors |
| JP5996532B2 (ja) | 2010-07-15 | 2016-09-21 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 有害生物防除剤としての新規複素環式化合物 |
| JP6100687B2 (ja) | 2010-08-31 | 2017-03-22 | ダウ アグロサイエンシィズ エルエルシー | 農薬組成物 |
| JP2012082186A (ja) | 2010-09-15 | 2012-04-26 | Bayer Cropscience Ag | 殺虫性アリールピロリジン類 |
| BR112013009823A2 (pt) | 2010-10-22 | 2016-07-05 | Bayer Ip Gmbh | novos compostos heterocíclicos como pesticidas |
| PH12013500886A1 (en) | 2010-11-03 | 2019-07-03 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
| CN103619171B (zh) | 2010-11-03 | 2015-11-25 | 陶氏益农公司 | 杀虫组合物和与其相关的方法 |
| 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 |
| JPWO2012102387A1 (ja) | 2011-01-27 | 2014-07-03 | 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 |
| BR112013020282A2 (pt) | 2011-02-09 | 2017-07-18 | Nissan Chemical Ind Ltd | derivado pirazol e agente de controle |
| JP2012188418A (ja) | 2011-02-22 | 2012-10-04 | Nissan Chem Ind Ltd | トリアゾ−ル誘導体及び有害生物防除剤 |
| US20120220453A1 (en) | 2011-02-25 | 2012-08-30 | Dow Agrosciences Llc | Pesticidal compostions and processes related thereto |
| JP2013107867A (ja) | 2011-04-21 | 2013-06-06 | Nissan Chem Ind Ltd | ピラゾール誘導体及び有害生物防除剤 |
| WO2012147107A2 (en) | 2011-04-29 | 2012-11-01 | Msn Laboratories Limited | Novel & improved processes for the preparation of indoline derivatives and its pharmaceutical composition |
| EP2532661A1 (en) | 2011-06-10 | 2012-12-12 | Syngenta Participations AG | Novel insecticides |
| EP2540718A1 (en) | 2011-06-29 | 2013-01-02 | Syngenta Participations AG. | Novel insecticides |
| AR087119A1 (es) | 2011-07-12 | 2014-02-12 | Dow Agrosciences Llc | Composiciones plaguicidas y procesos relacionados |
| WO2013010946A2 (en) | 2011-07-15 | 2013-01-24 | Basf Se | Pesticidal methods using substituted 3-pyridyl thiazole compounds and derivatives for combating animal pests i |
| JP2013075871A (ja) | 2011-09-30 | 2013-04-25 | Nissan Chem Ind Ltd | チアゾール誘導体および有害生物防除剤 |
| JP2013082699A (ja) | 2011-09-30 | 2013-05-09 | Nissan Chem Ind Ltd | ピラゾール誘導体および有害生物防除剤 |
| JP2013082704A (ja) | 2011-09-30 | 2013-05-09 | Nissan Chem Ind Ltd | チアゾール誘導体および有害生物防除剤 |
| JP6027128B2 (ja) * | 2011-10-26 | 2016-11-16 | ダウ アグロサイエンシィズ エルエルシー | 有害生物防除組成物およびそれに関連した方法 |
| BR112014009391A2 (pt) | 2011-10-26 | 2017-04-18 | Dow Agrosciences Llc | dosagem faseada de clopidogrel |
| DE102011085492A1 (de) | 2011-10-31 | 2013-05-02 | Evonik Goldschmidt Gmbh | Neue aminogruppenhaltige Siloxane, Verfahren zu deren Herstellung und Anwendung |
| JP2013129651A (ja) | 2011-11-22 | 2013-07-04 | Nissan Chem Ind Ltd | チアゾール誘導体および有害生物防除剤 |
| JP2013129653A (ja) | 2011-11-22 | 2013-07-04 | Nissan Chem Ind Ltd | トリアゾ−ル誘導体および有害生物防除剤 |
| WO2013156433A1 (en) | 2012-04-17 | 2013-10-24 | Syngenta Participations Ag | Insecticidally active thiazole derivatives |
| WO2013156431A1 (en) | 2012-04-17 | 2013-10-24 | Syngenta Participations Ag | Pesticidally active pyridyl- and pyrimidyl- substituted thiazole and thiadiazole derivatives |
| CN104822266B (zh) | 2012-04-27 | 2017-12-05 | 陶氏益农公司 | 杀虫组合物和与其相关的方法 |
| BR112014029957B1 (pt) | 2012-06-04 | 2019-01-15 | Dow Agrosciences Llc | processos para produzir determinados 2-(piridina-3-il)tiazóis |
| HK1208674A1 (en) | 2012-06-04 | 2016-03-11 | 美国陶氏益农公司 | Processes to produce certain 2-(pyridine-3-yl)thiazoles |
| US9108932B2 (en) | 2013-03-13 | 2015-08-18 | Dow Agrosciences Llc | Preparation of haloalkoxyarylhydrazines and intermediates therefrom |
| WO2015058028A1 (en) | 2013-10-17 | 2015-04-23 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| JP2016536295A (ja) | 2013-10-17 | 2016-11-24 | ダウ アグロサイエンシィズ エルエルシー | 有害生物防除性化合物の製造方法 |
| US9085564B2 (en) | 2013-10-17 | 2015-07-21 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| CN105636440A (zh) | 2013-10-17 | 2016-06-01 | 美国陶氏益农公司 | 制备杀虫化合物的方法 |
| WO2015058022A1 (en) | 2013-10-17 | 2015-04-23 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| US9174962B2 (en) | 2013-10-17 | 2015-11-03 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| WO2015058024A1 (en) | 2013-10-17 | 2015-04-23 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| EP3174856A4 (en) | 2014-07-31 | 2018-01-10 | Dow AgroSciences LLC | Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine |
| JP2017523168A (ja) | 2014-07-31 | 2017-08-17 | ダウ アグロサイエンシィズ エルエルシー | ３−（３−クロロ−１ｈ−ピラゾール−１−イル）ピリジンの製造方法 |
| BR112017000565A2 (pt) | 2014-07-31 | 2017-11-07 | Dow Agrosciences Llc | processo para a preparação de 3-(3-cloro-1h-pirazol-1-il)piridina |
| EP3183238A4 (en) | 2014-08-19 | 2018-01-10 | Dow AgroSciences LLC | Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine |
| BR112017004613A2 (pt) | 2014-09-12 | 2017-12-05 | Dow Agrosciences Llc | processo para a preparação de 3-(3-cloro-1h-pirazol-1-il)piridina |
-
2014
- 2014-10-17 WO PCT/US2014/061027 patent/WO2015058028A1/en not_active Ceased
- 2014-10-17 KR KR1020167012456A patent/KR20160072154A/ko not_active Withdrawn
- 2014-10-17 EP EP14854656.7A patent/EP3057430A4/en not_active Withdrawn
- 2014-10-17 MX MX2016004942A patent/MX2016004942A/es unknown
- 2014-10-17 CA CA2925595A patent/CA2925595A1/en not_active Abandoned
- 2014-10-17 JP JP2016523965A patent/JP2016539092A/ja active Pending
- 2014-10-17 CN CN201480056340.4A patent/CN105636441B/zh not_active Expired - Fee Related
- 2014-10-17 US US14/517,587 patent/US9102654B2/en not_active Expired - Fee Related
-
2015
- 2015-05-21 US US14/718,627 patent/US9255083B2/en not_active Expired - Fee Related
-
2016
- 2016-01-06 US US14/988,786 patent/US9434712B2/en not_active Expired - Fee Related
- 2016-04-04 IL IL244885A patent/IL244885A0/en unknown
- 2016-07-29 US US15/223,142 patent/US9670178B2/en not_active Expired - Fee Related
-
2017
- 2017-04-27 US US15/498,691 patent/US9862702B2/en not_active Expired - Fee Related
- 2017-12-08 US US15/835,795 patent/US20180099945A1/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20200011959A (ko) * | 2017-05-26 | 2020-02-04 | 다우 아그로사이언시즈 엘엘씨 | 피라졸 아민 반응성 결정화 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20150252018A1 (en) | 2015-09-10 |
| WO2015058028A8 (en) | 2015-12-30 |
| US9670178B2 (en) | 2017-06-06 |
| EP3057430A4 (en) | 2017-09-13 |
| EP3057430A1 (en) | 2016-08-24 |
| US9255083B2 (en) | 2016-02-09 |
| IL244885A0 (en) | 2016-05-31 |
| US20160332987A1 (en) | 2016-11-17 |
| WO2015058028A1 (en) | 2015-04-23 |
| US9434712B2 (en) | 2016-09-06 |
| CA2925595A1 (en) | 2015-04-23 |
| CN105636441B (zh) | 2018-06-15 |
| US20180099945A1 (en) | 2018-04-12 |
| JP2016539092A (ja) | 2016-12-15 |
| US20150112077A1 (en) | 2015-04-23 |
| MX2016004942A (es) | 2016-06-28 |
| US20170226078A1 (en) | 2017-08-10 |
| CN105636441A (zh) | 2016-06-01 |
| US9102654B2 (en) | 2015-08-11 |
| US20160137625A1 (en) | 2016-05-19 |
| US9862702B2 (en) | 2018-01-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR20160072154A (ko) | 살충성 화합물의 제조 방법 | |
| JP6487426B2 (ja) | 有害生物防除化合物の調製法 | |
| US9580405B2 (en) | Processes for the preparation of pesticidal compounds | |
| KR20160074542A (ko) | 살충성 화합물의 제조 방법 | |
| KR20160075565A (ko) | 살충성 화합물의 제조 방법 | |
| KR20170042714A (ko) | 3-(3-클로로-1h-피라졸-1-일)피리딘의 제조 방법 | |
| KR20160074540A (ko) | 살충성 화합물의 제조 방법 | |
| KR20160074541A (ko) | 살충성 화합물의 제조 방법 | |
| KR20170058388A (ko) | 3-(3-클로로-1h-피라졸-1-일)피리딘의 제조 방법 | |
| JP2007515444A (ja) | 殺菌効果を有する置換複素環式アミド | |
| EP1360176B1 (en) | Pyrrolecarboxamides for use as fungicides | |
| CN121850946A (zh) | 一种具有环丙烷羧酸吡唑酯类结构的化合物及其应用 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20160512 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |