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- Withdrawn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
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- 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
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- 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
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- 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)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (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
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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 (OSRAM) |
| EP (1) | EP3057430A4 (OSRAM) |
| JP (1) | JP2016539092A (OSRAM) |
| KR (1) | KR20160072154A (OSRAM) |
| CN (1) | CN105636441B (OSRAM) |
| CA (1) | CA2925595A1 (OSRAM) |
| IL (1) | IL244885A0 (OSRAM) |
| MX (1) | MX2016004942A (OSRAM) |
| WO (1) | WO2015058028A1 (OSRAM) |
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 (222)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP3057431A4 (en) | 2013-10-17 | 2017-04-05 | Dow AgroSciences LLC | Processes for the preparation of pesticidal compounds |
| KR20160075565A (ko) | 2013-10-17 | 2016-06-29 | 다우 아그로사이언시즈 엘엘씨 | 살충성 화합물의 제조 방법 |
| MX2016004946A (es) | 2013-10-17 | 2016-06-28 | Dow Agrosciences Llc | Procesos para la preparacion de compuestos plaguicidas. |
| WO2015058024A1 (en) | 2013-10-17 | 2015-04-23 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| CA2925873A1 (en) | 2013-10-17 | 2015-04-23 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| JP2016536296A (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 |
| WO2015058028A1 (en) | 2013-10-17 | 2015-04-23 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| CN106470976A (zh) | 2014-07-31 | 2017-03-01 | 美国陶氏益农公司 | 制备3‑(3‑氯‑1h‑吡唑‑1‑基)吡啶的方法 |
| AR098110A1 (es) | 2014-07-31 | 2016-05-04 | Dow Agrosciences Llc | Proceso para la preparación de 3-(3-cloro-1h-pirazol-1-il)piridina |
| US9029555B1 (en) | 2014-07-31 | 2015-05-12 | Dow Agrosciences Llc | Process for the preparation of 3-(3-chloro-1H-pyrazol-1-yl)pyridine |
| BR112017002735A2 (pt) | 2014-08-19 | 2017-12-19 | Dow Agrosciences Llc | processo para a preparação de 3-(3-cloro-1h-pirazol-1-il)piridina |
| KR20170058388A (ko) | 2014-09-12 | 2017-05-26 | 다우 아그로사이언시즈 엘엘씨 | 3-(3-클로로-1h-피라졸-1-일)피리딘의 제조 방법 |
| WO2017072039A1 (de) | 2015-10-26 | 2017-05-04 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| WO2017093180A1 (de) | 2015-12-01 | 2017-06-08 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| AU2016363632A1 (en) | 2015-12-03 | 2018-06-07 | Bayer Cropscience Aktiengesellschaft | Mesoionic halogenated 3-(acetyl)-1-((1,3-thiazol-5-yl)methyl)-1h-imidazo(1,2-a)pyridin-4-ium-2-olate derivatives and related compounds as insecticides |
| CA3013962A1 (en) | 2016-02-11 | 2017-08-17 | Bayer Cropscience Aktiengesellschaft | Substituted 2-(het)aryl-imidazolyl-carboxyamides as pest control agents |
| MX2018009809A (es) | 2016-02-11 | 2018-09-10 | Bayer Cropscience Ag | 2-oximidazolilcarboxamidas sustituidas como plaguicidas. |
| WO2017144341A1 (de) | 2016-02-23 | 2017-08-31 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| JP2019510020A (ja) | 2016-03-15 | 2019-04-11 | 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 | 害虫を防除するための置換スルホニルアミド類 |
| BR112018068681A2 (pt) | 2016-03-16 | 2019-01-15 | Bayer Cropscience Ag | derivados de n-(cianobenzil)-6-(ciclopropil-carbonilamino)-4-(fenil)-piridina-2-carboxamida e compostos relacionados como pesticidas e agentes de proteção de plantas |
| WO2017174414A1 (de) | 2016-04-05 | 2017-10-12 | Bayer Cropscience Aktiengesellschaft | Naphthalin-derivate als schädlingsbekämpfungsmittel |
| SG11201808214TA (en) | 2016-04-15 | 2018-10-30 | Bayer Animal Health Gmbh | Pyrazolopyrimidine derivatives |
| KR20180135956A (ko) | 2016-04-25 | 2018-12-21 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 해충 방제제로서의 치환된 2-알킬이미다졸릴-카르복스아미드 |
| 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 |
| WO2017198451A1 (en) | 2016-05-17 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in small grain cereals such as wheat and rice |
| WO2017198454A1 (en) | 2016-05-17 | 2017-11-23 | Bayer Cropscience Nv | Method for increasing yield in cotton |
| 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 |
| CA3031139A1 (en) | 2016-07-19 | 2018-01-25 | Bayer Cropscience Aktiengesellschaft | Condensed bicyclic heterocycle derivatives as pest control agents |
| EP3490363A1 (en) | 2016-07-29 | 2019-06-05 | Bayer CropScience Aktiengesellschaft | Formulation comprising a beneficial p. bilaii strain and talc for use in seed treatment |
| KR20190037305A (ko) | 2016-08-10 | 2019-04-05 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 해충 방제제로서의 치환된 2-헤테로시클릴 이미다졸릴-카르복스아미드 |
| KR102419244B1 (ko) | 2016-08-15 | 2022-07-08 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 해충 방제제로서의 축합 바이시클릭 헤테로사이클 유도체 |
| MX2019003136A (es) | 2016-09-19 | 2019-07-18 | Bayer Cropscience Ag | Derivados de pirazolo [1,5-a]piridina y su uso como pesticidas. |
| AU2017340690B2 (en) | 2016-10-06 | 2021-05-20 | Bayer Cropscience Aktiengesellschaft | 2-(Het)aryl-substituted condensed bicyclic heterocycle derivatives as pest control agents |
| 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 |
| PL3538512T3 (pl) | 2016-11-11 | 2021-11-22 | Bayer Animal Health Gmbh | Nowe pochodne chinolino-3-karboksyamidu o działaniu przeciw robakom pasożytniczym |
| WO2018095953A1 (de) | 2016-11-23 | 2018-05-31 | Bayer Cropscience Aktiengesellschaft | 2-[3-(alkylsulfonyl)-2h-indazol-2-yl]-3h-imidazo[4,5-b]pyridin-derivate und ähnliche verbindungen als schädlingsbekämpfungsmittel |
| JP2020502168A (ja) | 2016-12-16 | 2020-01-23 | 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 | 殺有害生物剤としてのチアジアゾール誘導体 |
| BR112019012262A2 (pt) | 2016-12-16 | 2019-12-03 | Bayer Ag | imidazopiridinas mesoiônicas para uso como inseticidas |
| WO2018125816A1 (en) | 2016-12-29 | 2018-07-05 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| WO2018125817A1 (en) | 2016-12-29 | 2018-07-05 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| CN110139853B (zh) | 2016-12-29 | 2023-06-16 | 美国陶氏益农公司 | 用于制备杀有害生物化合物的方法 |
| US11058115B2 (en) | 2017-01-10 | 2021-07-13 | Bayer Aktiengesellschaft | Heterocycle derivatives as pesticides |
| EP3568395A1 (de) | 2017-01-10 | 2019-11-20 | Bayer Aktiengesellschaft | Heterocyclen-derivate als schädlingsbekämpfungsmittel |
| 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 |
| KR20190141194A (ko) | 2017-04-21 | 2019-12-23 | 바이엘 악티엔게젤샤프트 | 살곤충제로서의 메소이온성 이미다조피리딘 |
| CN110582503B (zh) | 2017-04-24 | 2022-05-31 | 拜耳公司 | 作为有害物防治剂的稠合双环杂环化合物衍生物 |
| 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 |
| DK3585791T3 (da) | 2017-04-27 | 2024-12-02 | Elanco Animal Health Gmbh | Nye bicykliske pyrazolderivater |
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| JP7119004B2 (ja) | 2017-05-02 | 2022-08-16 | バイエル・アクチエンゲゼルシヤフト | 有害生物防除剤としての２－（ヘタ）アリール置換縮合二環式ヘテロ環式誘導体 |
| BR112019023030A2 (pt) | 2017-05-03 | 2020-06-02 | Bayer Aktiengesellschaft | Sililmetilfenoxiquinolinas trissubstituídas e análogos |
| US20200231607A1 (en) | 2017-05-03 | 2020-07-23 | Bayer Aktiengesellschaft | Trisubstitutedsilylheteroaryloxyquinolines and analogues |
| WO2018202715A1 (en) | 2017-05-03 | 2018-11-08 | Bayer Aktiengesellschaft | Trisubstitutedsilylbenzylbenzimidazoles and analogues |
| WO2018202525A1 (en) | 2017-05-04 | 2018-11-08 | Bayer Cropscience Aktiengesellschaft | Phenoxyethanamine derivatives for controlling pests |
| BR112019023152B1 (pt) | 2017-05-04 | 2023-10-03 | Discovery Purchaser Corporation | Compostos heterocíclicos derivados de 2-{[2-(feniloximetil) piridina-5-il] oxi}-etanamina, seus usos e seus intermediários, formulações, e método para controle de pragas |
| US11485733B2 (en) | 2017-06-30 | 2022-11-01 | Bayer Animal Health Gmbh | Azaquinoline derivatives |
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-
2014
- 2014-10-17 WO PCT/US2014/061027 patent/WO2015058028A1/en not_active Ceased
- 2014-10-17 EP EP14854656.7A patent/EP3057430A4/en not_active Withdrawn
- 2014-10-17 KR KR1020167012456A patent/KR20160072154A/ko not_active Withdrawn
- 2014-10-17 US US14/517,587 patent/US9102654B2/en not_active Expired - Fee Related
- 2014-10-17 MX MX2016004942A patent/MX2016004942A/es unknown
- 2014-10-17 CN CN201480056340.4A patent/CN105636441B/zh not_active Expired - Fee Related
- 2014-10-17 CA CA2925595A patent/CA2925595A1/en not_active Abandoned
- 2014-10-17 JP JP2016523965A patent/JP2016539092A/ja active Pending
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2015
- 2015-05-21 US US14/718,627 patent/US9255083B2/en not_active Expired - Fee Related
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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 |
|---|---|
| US9255083B2 (en) | 2016-02-09 |
| CN105636441A (zh) | 2016-06-01 |
| JP2016539092A (ja) | 2016-12-15 |
| US20160332987A1 (en) | 2016-11-17 |
| CA2925595A1 (en) | 2015-04-23 |
| US9670178B2 (en) | 2017-06-06 |
| IL244885A0 (en) | 2016-05-31 |
| EP3057430A4 (en) | 2017-09-13 |
| EP3057430A1 (en) | 2016-08-24 |
| WO2015058028A1 (en) | 2015-04-23 |
| WO2015058028A8 (en) | 2015-12-30 |
| US9102654B2 (en) | 2015-08-11 |
| MX2016004942A (es) | 2016-06-28 |
| US9862702B2 (en) | 2018-01-09 |
| US20170226078A1 (en) | 2017-08-10 |
| CN105636441B (zh) | 2018-06-15 |
| US20180099945A1 (en) | 2018-04-12 |
| US9434712B2 (en) | 2016-09-06 |
| US20150252018A1 (en) | 2015-09-10 |
| US20150112077A1 (en) | 2015-04-23 |
| US20160137625A1 (en) | 2016-05-19 |
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