CN1004272B - Pyrazoline insecticides - Google Patents
Pyrazoline insecticides Download PDFInfo
- Publication number
- CN1004272B CN1004272B CN85107882.6A CN85107882A CN1004272B CN 1004272 B CN1004272 B CN 1004272B CN 85107882 A CN85107882 A CN 85107882A CN 1004272 B CN1004272 B CN 1004272B
- Authority
- CN
- China
- Prior art keywords
- pyrazoline
- halogen
- carboxylamide
- low alkyl
- alkyl group
- 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.)
- Expired
Links
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 title claims abstract description 46
- 239000002917 insecticide Substances 0.000 title abstract description 15
- 239000000126 substance Substances 0.000 claims abstract description 46
- 238000000034 method Methods 0.000 claims abstract description 20
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 10
- 239000000575 pesticide Substances 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims description 64
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 47
- 239000001257 hydrogen Substances 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 45
- 150000002367 halogens Chemical class 0.000 claims description 41
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 125000002521 alkyl halide group Chemical group 0.000 claims description 24
- 230000000749 insecticidal effect Effects 0.000 claims description 20
- 239000007788 liquid Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 150000003219 pyrazolines Chemical class 0.000 claims description 10
- 241000238631 Hexapoda Species 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000002689 soil Substances 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 239000005864 Sulphur Substances 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 25
- 239000004480 active ingredient Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract 1
- -1 for example Inorganic materials 0.000 description 67
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 35
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 21
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 14
- 235000008504 concentrate Nutrition 0.000 description 12
- 239000012141 concentrate Substances 0.000 description 12
- 125000001207 fluorophenyl group Chemical group 0.000 description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 230000006837 decompression Effects 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 9
- HRMHWJBTJOGTGG-UHFFFAOYSA-N FC1=CC=C(C=C1)N1NC=CC1 Chemical class FC1=CC=C(C=C1)N1NC=CC1 HRMHWJBTJOGTGG-UHFFFAOYSA-N 0.000 description 8
- 239000000470 constituent Substances 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- IANQTJSKSUMEQM-UHFFFAOYSA-N benzofuran Natural products C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- HQKKXJTWSRPAHD-UHFFFAOYSA-N 2-(4-chlorophenyl)-1,3-dihydropyrazole Chemical class ClC1=CC=C(C=C1)N1NC=CC1 HQKKXJTWSRPAHD-UHFFFAOYSA-N 0.000 description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241000409991 Mythimna separata Species 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- PPVUWDCETZMPLT-UHFFFAOYSA-N 1,3-dihydropyrazole-2-carboxamide Chemical class NC(=O)N1CC=CN1 PPVUWDCETZMPLT-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- KSXUYLPLFRMQRY-UHFFFAOYSA-N 4-(4-fluorophenyl)-1-methylpyrazole Chemical compound C1=NN(C)C=C1C1=CC=C(F)C=C1 KSXUYLPLFRMQRY-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 241000519878 Anomala rufocuprea Species 0.000 description 2
- 235000016068 Berberis vulgaris Nutrition 0.000 description 2
- 241000335053 Beta vulgaris Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 241000255993 Trichoplusia ni Species 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000004533 benzofuran-5-yl group Chemical group O1C=CC2=C1C=CC(=C2)* 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 229940072033 potash Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 2
- 125000002755 pyrazolinyl group Chemical group 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- DOMQFIFVDIAOOT-ROUUACIJSA-N (2S,3R)-N-[4-(2,6-dimethoxyphenyl)-5-(5-methylpyridin-3-yl)-1,2,4-triazol-3-yl]-3-(5-methylpyrimidin-2-yl)butane-2-sulfonamide Chemical compound COC1=C(C(=CC=C1)OC)N1C(=NN=C1C=1C=NC=C(C=1)C)NS(=O)(=O)[C@@H](C)[C@H](C)C1=NC=C(C=N1)C DOMQFIFVDIAOOT-ROUUACIJSA-N 0.000 description 1
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
- UKGJZDSUJSPAJL-YPUOHESYSA-N (e)-n-[(1r)-1-[3,5-difluoro-4-(methanesulfonamido)phenyl]ethyl]-3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CCCC1=NC(C(F)(F)F)=CC=C1\C=C\C(=O)N[C@H](C)C1=CC(F)=C(NS(C)(=O)=O)C(F)=C1 UKGJZDSUJSPAJL-YPUOHESYSA-N 0.000 description 1
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
- JLGADZLAECENGR-UHFFFAOYSA-N 1,1-dibromo-1,2,2,2-tetrafluoroethane Chemical class FC(F)(F)C(F)(Br)Br JLGADZLAECENGR-UHFFFAOYSA-N 0.000 description 1
- APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 1
- WYUJZLSRJRHRSK-UHFFFAOYSA-N 2,2,3,3-tetrafluoro-1-benzofuran-5-amine Chemical compound NC1=CC=C2OC(F)(F)C(F)(F)C2=C1 WYUJZLSRJRHRSK-UHFFFAOYSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
- YGYGASJNJTYNOL-CQSZACIVSA-N 3-[(4r)-2,2-dimethyl-1,1-dioxothian-4-yl]-5-(4-fluorophenyl)-1h-indole-7-carboxamide Chemical compound C1CS(=O)(=O)C(C)(C)C[C@@H]1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(F)=CC=3)C=C12 YGYGASJNJTYNOL-CQSZACIVSA-N 0.000 description 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 1
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- VJPPLCNBDLZIFG-ZDUSSCGKSA-N 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-5-fluoro-2,3-dimethyl-1H-indole-7-carboxamide Chemical compound C(C#CC)(=O)N[C@@H]1CN(CCC1)C1=C2C(=C(NC2=C(C=C1F)C(=O)N)C)C VJPPLCNBDLZIFG-ZDUSSCGKSA-N 0.000 description 1
- YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 1
- XYWIPYBIIRTJMM-IBGZPJMESA-N 4-[[(2S)-2-[4-[5-chloro-2-[4-(trifluoromethyl)triazol-1-yl]phenyl]-5-methoxy-2-oxopyridin-1-yl]butanoyl]amino]-2-fluorobenzamide Chemical compound CC[C@H](N1C=C(OC)C(=CC1=O)C1=C(C=CC(Cl)=C1)N1C=C(N=N1)C(F)(F)F)C(=O)NC1=CC(F)=C(C=C1)C(N)=O XYWIPYBIIRTJMM-IBGZPJMESA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
- KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
- BOFRXDMCQRTGII-UHFFFAOYSA-N 619-08-9 Chemical compound OC1=CC=C([N+]([O-])=O)C=C1Cl BOFRXDMCQRTGII-UHFFFAOYSA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
- ZRPZPNYZFSJUPA-UHFFFAOYSA-N ARS-1620 Chemical compound Oc1cccc(F)c1-c1c(Cl)cc2c(ncnc2c1F)N1CCN(CC1)C(=O)C=C ZRPZPNYZFSJUPA-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000462639 Epilachna varivestis Species 0.000 description 1
- GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical class CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- FEYNFHSRETUBEM-UHFFFAOYSA-N N-[3-(1,1-difluoroethyl)phenyl]-1-(4-methoxyphenyl)-3-methyl-5-oxo-4H-pyrazole-4-carboxamide Chemical compound COc1ccc(cc1)N1N=C(C)C(C(=O)Nc2cccc(c2)C(C)(F)F)C1=O FEYNFHSRETUBEM-UHFFFAOYSA-N 0.000 description 1
- IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
- RCEAADKTGXTDOA-UHFFFAOYSA-N OS(O)(=O)=O.CCCCCCCCCCCC[Na] Chemical compound OS(O)(=O)=O.CCCCCCCCCCCC[Na] RCEAADKTGXTDOA-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241001521235 Spodoptera eridania Species 0.000 description 1
- 241000256247 Spodoptera exigua Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 241000255985 Trichoplusia 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
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 238000009835 boiling Methods 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
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- DGLFSNZWRYADFC-UHFFFAOYSA-N chembl2334586 Chemical compound C1CCC2=CN=C(N)N=C2C2=C1NC1=CC=C(C#CC(C)(O)C)C=C12 DGLFSNZWRYADFC-UHFFFAOYSA-N 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000018927 edible plant Nutrition 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 231100000225 lethality Toxicity 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- FMASTMURQSHELY-UHFFFAOYSA-N n-(4-fluoro-2-methylphenyl)-3-methyl-n-[(2-methyl-1h-indol-4-yl)methyl]pyridine-4-carboxamide Chemical compound C1=CC=C2NC(C)=CC2=C1CN(C=1C(=CC(F)=CC=1)C)C(=O)C1=CC=NC=C1C FMASTMURQSHELY-UHFFFAOYSA-N 0.000 description 1
- NNKPHNTWNILINE-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-4-methyl-5-[3-[[1-[2-[2-(methylamino)ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]benzamide Chemical compound CNCCOC1=CC=CC=C1C1(NC=2C(N(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)C=CN=2)=O)CC1 NNKPHNTWNILINE-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 150000007984 tetrahydrofuranes Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention relates to a catalyst containing a chemical formula
Description
The present invention relates to the field of the composition of chemicals with biological effect; Say that more properly it relates to some novel preparation method for pyrazolines, the technical process of producing these insecticides and intermediate, contain the insecticidal compositions of pyrazoline and be used for the using method of pyrazoline of pest control.
Pyrazoline is the heterocyclic compound that has five atoms in its ring, and it has the schematic diagram of following chemical formula and annular atoms Position Number:
People know in this technical field of insecticide, and the derivative of some 1-carbamoylpyrazolines is an insecticide.For example United States Patent (USP) 4,174, just revealed the insecticidal activity of 1-carbamoylpyrazolines in 393, and this 1-carbamoylpyrazolines also can have the phenyl substituent in the position 3 of pyrazoline ring and position 4.
The invention provides the pyrazoline that some have following structural formula, they have shown described insecticidal activity, and this structural formula is:
Wherein, R
AChemical formula be
, the R here
A' be select from hydrogen, halogen, low alkyl group, lower alkoxy, rudimentary halogen alkoxyl, rudimentary alkynyloxy group and rudimentary alkylhalide group; Or
, wherein X is that chemical formula is
O-(CR '
BAR '
BB) a-Oa '
Bridge connector, a here is 1～3, a ' is 0 or 1, a+a ' is at least 2 but be not more than 3, R '
AAAnd R '
ABBe at random select from hydrogen, halogen and low alkyl group, and R '
ACBe select from hydrogen, halogen low alkyl group, lower alkoxy, rudimentary halogen alkoxyl and rudimentary alkylhalide group; R
BBe that chemical formula is
4-or 5-substituting group, R wherein
B' be select from hydrogen, halogen, low alkyl group, lower alkoxy and rudimentary alkylhalide group; Or
Y wherein is that chemical formula is
O-(CR '
BAR '
BB) b-O
b'
Bridge connector, the b here is 1～3, b ' is 0 or 1, b+b ' is at least 2 but be not more than 3, R '
BAAnd R '
BBBe at random select from hydrogen, halogen and low alkyl group,
R '
BCBe select from hydrogen, halogen, low alkyl group, lower alkoxy, rudimentary halogen alkoxyl and rudimentary alkylhalide group;
R
CChemical formula be
, R wherein
DBe select from hydrogen and low alkyl group, and R
EBe from hydrogen, low alkyl group, lower alkoxy, rudimentary halogen alkoxyl, rudimentary alkylhalide group, cyano group, nitro ,-NR
FR
G(R here,
FAnd R
GBe low alkyl group arbitrarily) and-SO
nR
H(the R here
HBe low alkyl group, n is 0～3) in select; Or
, Z wherein is a chemical formula
O-(CR '
CAR '
CB) c-Oc '
Bridge connector, the c here is 1～3, c ' is 0 or 1, c+c ' is at least 2 but be not more than 3, R '
CAAnd R '
CBBe at random select from hydrogen, halogen and low alkyl group, in some compound, when c is 1 and c ' when being 1, R '
CAAnd R '
CBThe two can not all be a hydrogen, and R '
CCBe select from hydrogen, halogen, low alkyl group, lower alkoxy, rudimentary halogen alkoxyl and rudimentary alkylhalide group;
R
NBe hydrogen or low alkyl group; And V and W are at random oxygen or sulphur.
" halogen " or " halogen " these terms are meant fluorine, chlorine or bromine here when they are used." rudimentary " this term of modifying " alkyl ", " alkoxyl ", " alkynyloxy group " and homologue thereof is meant 1～6 but the chain of the hydrocarbon of the straight chain of 1～4 carbon atom or side chain preferably; " halogen " this word that links to each other with other term is meant that one or more hydrogen atoms are replaced by halogen.
In the said in front pyrazoline, W is that those compounds of oxygen relatively are applicable to multiple application comparatively speaking, especially as R '
AWhen being the 4-substituting group, preferably select halogen, for example, nitrogen or fluorine, or rudimentary halogen alkoxyl, difluoro-methoxy for example, R
BBe that substituent those pyrazolines of 4-are normally more active than the pyrazoline that corresponding 5-replaces, and R wherein
BBe have substituent R '
BThose compounds of phenyl then noticeable especially.From this angle, then comparatively ideal situation is R '
BBe 4-substituting group, especially halogen, for example chlorine or fluorine.
With regard to R
cAnd opinion, then the most attractive insecticide is normally from some specific compound deriving, and these compounds contain 2,3-dihydro-2,2-dimethyl benzofuran-5-base, 2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-base, 2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-6-base, 2,2-two fluoro-1,3-benzo dioxole-5-base, or 2,2-dimethyl-1,3-benzo dioxole-5-base group, or 4-Phenoxyphenyl group.In the back in this case, it would be desirable R
DBe hydrogen, and R is the 4-substituting group, especially rudimentary halogen alkoxyl.
Pyrazoline of the present invention with significant insecticidal activity comprises, for example, 3-(4-difluoro-methoxy phenyl)-N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-4-phenylpyrrazolin-1-Carboxylamide (Carboxamide), 3, two (4-the fluorophenyl)-N-(2 of 4-, 3-dihydro-2,2-dimethyl benzofuran-5-yl) pyrazoline 1-Carboxylamide, N-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-yl)-3-(4-difluoro-methoxy phenyl)-4-phenylpyrrazolin-1-Carboxylamide, N-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-3-(4-difluoro-methoxy phenyl)-N-methyl-4-phenylpyrrazolin-1-Carboxylamide, 3, two (4-the chlorphenyl)-N-(2 of 4-, 2-dimethyl-1,3-benzo dioxole) pyrazoline-1-Carboxylamide, N-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-3, two (4-fluorophenyl) pyrazolines of 4--1-Carboxylamide.The 3-(4-chlorphenyl)-N-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-and the 4-(4-fluorophenyl) pyrazoline-1-Carboxylamide, 3-(4-difluoro-methoxy phenyl)-N-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-yl)-N-methyl-4-phenylpyrrazolin-1-Carboxylamide, the 3-(4-chlorphenyl)-N-(4-(4-difluoromethoxy phenyl oxygen base) phenyl)-4-phenylpyrrazolin-1-Carboxylamide, N-(4-(4-difluoromethoxy phenyl oxygen base) phenyl)-3-(4-difluoro-methoxy phenyl)-the 4-(4-fluorophenyl) pyrazoline-1-Carboxylamide, 3-(4-difluoro-methoxy phenyl)-the 4-(4-fluorophenyl)-N-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-yl) pyrazoline-1-Carboxylamide, 3-(4-difluoro-methoxy phenyl)-the 4-(4-fluorophenyl)-N-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-6-yl) pyrazoline-1-Carboxylamide, the 4-(4-chlorphenyl)-N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-3-phenylpyrrazolin-1-Carboxylamide, the 3-(4-chlorphenyl)-the 4-(4-fluorophenyl)-N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl) pyrazoline-1-Carboxylamide, 3-(4-difluoro-methoxy phenyl)-the 4-(4-fluorophenyl)-N-(2,3-dihydro-2-2-dimethyl benzofuran-5-yl) pyrazoline-1-Carboxylamide and 4-(4-chlorphenyl)-3-(4-difluoro-methoxy phenyl)-N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl) pyrazoline-1-Carboxylamide.
Similarly, also comprise some insecticidal compositions in the works in expection of the present invention, at least a foregoing pyrazoline that these mixtures contain is a certain amount of (reaching insecticidal effect), and it with a kind of agricultural on acceptable carrier mix mutually.In addition, the present invention also comprises the method for pest control, and this method comprises the described pyrazoline of at least a * face of a certain amount of (reaching insecticidal effect) is applied to the place that need carry out pest control.
Pyrazoline of the present invention can be made through a kind of like this method on the pyrazoline that suitably replaces by suitable aromatic isocyanates or isothiocyanate being coupled to, and in other words, a technical process in the scope of the invention is as follows:
Thereby the method that this product can have been known by people and produced the pyrazoline of corresponding N-alkylization by alkylation.
Through the pyrazoline starting material that suitably replaces is material known to the general people.This requisite isocyanates and isothiocyanate can be produced from corresponding amine.A certain amount of amine can have been bought on market.Other interested amine also can prepare by the method described in the following example.
Example 1
The 3-(4-chlorphenyl)-N-(4-(4-chlorophenoxy) phenyl)-4-phenylpyrrazolin-1-Carboxylamide
In the nitrogen protection atmosphere of drying, the process stirred mixture that the 4-chlorophenol of a kind of 4-fluoronitrobenzene by 10.9 grams (0.077 gram molecule), 9.95 grams (0.077 gram molecule) and the potash of 11.8 grams (0.085 gram molecule) are constituted in 175 milliliters dimethyl sulfoxide (DMSO) is subjected to heating and reaches two days under 70 ℃ temperature.Then, reactant mixture is cooled off and is filtered.The filtered fluid water dilutes, and is diluted to volume after the dilution always and is 1 and be upgraded to and end.And then this mixture is extracted with three strands 200 milliliters ether.The ether extration thing elder generation water that has mixed is washed with moisture saturated nacl aqueous solution again then.Be placed on the anhydrous sodium sulfate in addition dryly through the extract of washing again, and filter.At last, under the condition of decompression, this filtered fluid is evaporated the 4-(4-chlorophenoxy that has just obtained 13.5 grams) nitrobenzene (fusing point is 67～70 ℃).
4-(4-chlorophenoxy to 13.5 grams (0.054 gram molecule)) nitrobenzene carries out the 4-(4-chlorophenoxy that hydrogenation reaction has just produced quantitative yield with the platinum oxide of catalytic amount (0.15 gram) in 250 milliliters oxolane) aniline.
The solution of 0.43 milliliter of (0.0036 gram molecule) trichloromethyl chloro-formate (being in 20 milliliters of toluene) drop by drop is added to 0.75 gram (0.0034 gram molecule) 4-(4-chlorophenoxy through stirring) in the solution of aniline (being in 25 milliliters of toluene).After adding fully, this mixture just is heated three hours under 85 ℃ temperature.Then, this mixture just is cooled to room temperature, thereby and solvent just is evaporated and stays residue under the condition of decompression.Then, this residue is dissolved in again in 25 milliliters the ether.This solution also is 1.0 gram (0.0034 gram molecule) the 3-(4-chlorphenyls that drop by drop are added into through stirring)-slurry of 4-phenylpyrrazolin (being in the ether) in.Three triethylamines have been added into, and then at room temperature are stirred in this mixture to reach two days.Just obtained the 3-(4-chlorphenyl of 0.92 gram after solvent is evaporated from mixture)-N-(4-(4-chlorophenoxy) phenyl)-4-phenylpyrrazolin-1-Carboxylamide (fusing point is 158～161 ℃)
Analyze:
Calculated value C:66.92; H:4.22
Measured value C:66.06; H:4.95
Nuclear magnetic resonnance (nmr): 8.06PPm(CDCl
3)
Example 2
The 3-(4-chlorphenyl)-and N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-4-phenylpyrrazolin-1 Carboxylamide
Within one hour cycle, the ice-cold mixture of the concentrated sulfuric acid of a kind of 43 milliliters red fuming nitric acid (RFNA) and 50 milliliters is drop by drop joined 2 of 100.0 grams (0.67 gram molecule), 3-dihydro-2 goes in the 2-dimethyl benzofuran and makes temperature remain on 5 ℃.After adding fully, this mixture just is stirred 2.5 hours under 0 ℃.Then, this reactant mixture is introduced in the frozen water, and whole system is extracted with ether.In addition dry and filter to this extract on anhydrous magnesium chloride.By under the condition of decompression, this filtered fluid being evaporated the oil that has just made a kind of black.Come the oil of this black is purified by the column chromatography on silica gel, use the toluene of 9: 1 ratios and n-hexane to carry out elution again, thereby make 2 of 50.0 grams, 3-dihydro-2, at this moment 2-dimethyl-5-nitrobenzofuran has been solid.
In 250 milliliters methyl alcohol, come 2 of 20.0 grams (0.1 gram molecule), 3-dihydro-2 with the platinum oxide of catalytic amount (0.2 gram), 2-dimethyl-5-nitrobenzofuran carries out hydrogenation reaction, so just made the 5-amino-2 of 16.6 grams, 3-dihydro-2,2-dimethyl benzofuran.
0.43 the solution of milliliter (0.0036 gram molecule) trichloromethyl chloro-formate (being in 20 milliliters of toluene) is drop by drop joined 0.56 gram (0.0034 gram molecule) 5-amino-2 through stirring, 3-dihydro-2 is in the solution of 2-dimethyl benzofuran (being in 20 milliliters of toluene).After adding fully, just this mixture is carried out three hours backflow heating.Then, this mixture just is cooled to room temperature, and solvent just is evaporated under the condition of decompression, stays residue at last.This residue is dissolved in 25 milliliters the dry diethyl ether, and solution is at this moment just drop by drop added through 3-(4-chlorphenyls that stir, 1.0 grams (0.034 gram molecule))-mixture of 4-phenyl-pyrazole quinoline and three triethylamines (being in 25 milliliters of ether) in.This reactant mixture is at room temperature accepted about 18 hours stirring, and at this moment solid just is filtered out from mixture.Filter cake has become slurry and has obtained recovery after filtration in ethanol, thereby obtained the 3-(4-chlorphenyl of 0.47 gram)-N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-4-phenylpyrrazolin-1-Carboxylamide (fusing point is 160～162 ℃).
Analyze:
Calculated value C:70.00; H:5.43
Measured value C:69.50; H:3.36
Nuclear magnetic resonnance (nmr): 9.00ppm(DMSo-d
6)
Other product in this series that the employing similar techniques makes can be represented by following additional examples.Fusing point is represented with Celsius temperature.With=single (spectrum) line of corresponding this nuclear magnetic resonnance of NH proton (nmr), promptly the characteristic of these compounds also is given in some example.Except as otherwise noted, nuclear magnetic resonnance (nmr) solvent all is CDCl
3Elementary analysis has obtained expression in some instances.
Example 3
3,4-diphenyl-N-(4-Phenoxyphenyl) pyrazoline-1 Carboxylamide, fusing point is 184～188 ℃.9.17ppm（DMSo-d
6）
Example 4
N-(4-(4-chlorophenoxy) phenyl)-3,4-diphenylpyrazoline-1-Carboxylamide, fusing point is 146～149 ℃.8.83ppm（DMSo-d
6）
Example 5
The 3-(4-chlorphenyl)-the N-(4-Phenoxyphenyl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 163～166 ℃.8.03ppm
Example 6
The N-(4-Phenoxyphenyl)-and 4-phenyl-3-(4-trifluoromethyl) pyrazoline-1-Carboxylamide, 188～190 ℃ of fusing points.8.10ppm
Example 7
3, two (4-the chlorphenyl)-N-(4-Phenoxyphenyls of 4-) pyrazoline-1-Carboxylamide, fusing point is 189～193 ℃.8.20ppm（CDCl
3/DMSo-d
6）
Example 8
The 3-(4-chlorphenyl)-N-(3-methyl-4-Phenoxyphenyl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 151～157 ℃.9.13ppm（DMSo-d
3）
Example 9
The 3-(-4-chlorphenyl)-N-(4-(2-fluorophenoxy) phenyl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 153～155 ℃.8.16ppm
Example 10
The 3-(4-chlorphenyl)-N-(4-(3-fluorophenoxy) phenyl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 173～175 ℃.9.33ppm（DMSo-d
6）
Example 11
N-(4-(3-chlorophenoxy) phenyl)-the 3-(4-chlorphenyl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 169～175 ℃.9.30ppm（DMSo-d
6）
Example 12
The 3-(4-chlorphenyl)-N-(4-(4-fluorophenoxy) phenyl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 164～167 ℃.8.13ppm
Example 13
The 3-(4-chlorphenyl)-N-(4-(4-4-trifluoromethylphenopendant)-phenyl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 161～164 ℃.8.03ppm
Example 14
N-(4-(4-chlorophenoxy) phenyl)-3-(4-difluoro-methoxy phenyl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 103～107 ℃.8.00ppm
Example 15
3, two (4-the chlorphenyl)-N-(3-methyl of 4--4-Phenoxyphenyl)-pyrazoline-1-Carboxylamide, fusing point is 188～190 ℃.9.23ppm（DMSo-d
6）
Example 16
3, two (4-chlorphenyl)-N-(4-(2-fluorophenoxy) phenyl of 4-)-pyrazoline-1-Carboxylamide, fusing point is 160～162 ℃.8.10ppm
Example 17
3, two (4-chlorphenyl)-N-(4-(3-fluorophenoxy) phenyl of 4-)-pyrazoline-1-Carboxylamide, fusing point is 144～146 ℃.9.20ppm（DMSo-d
6）
Example 18
N-(4-(3-chlorophenoxy) phenyl)-3, two (4-the chlorphenyl)-pyrazolines of 4--1-Carboxylamide, fusing point is 135～140 ℃.9.30ppm（DMSo-d
6）
Example 19
3, two (4-chlorphenyl)-N-(4-(4-fluorophenoxy) phenyl of 4-)-pyrazoline-1-Carboxylamide, fusing point is 168～170 ℃.9.23ppm（DMSo-d
6）
Example 20
N-(4-(4-chlorophenoxy) phenyl)-3, two (4-the chlorphenyl)-pyrazolines of 4--1-Carboxylamide, fusing point is 154～156 ℃ of 9.30ppm(DMSo-d
6)
Example 21
3, two (4-chlorphenyl)-N-(4-(4-4-trifluoromethylphenopendant) phenyl of 4-)-pyrazoline-1-Carboxylamide, fusing point is 191～194 ℃.9.30ppm（DMSo-d
6）
Example 22
The 3-(4-chlorphenyl)-and 4-phenyl-N-(4-thiophenyl phenyl) pyrazoline-1-Carboxylamide, fusing point is 157～162 ℃.8.20ppm
Example 23
3, two (4-the chlorphenyl)-N-(4-thiophenyl phenyl of 4-) pyrazoline-1-Carboxylamide, fusing point is 169～171 ℃.8.20ppm
Example 24
3, two (4-the chlorphenyl)-N-(4-Phenoxyphenyls of 5-) pyrazoline-1-Carboxylamide, fusing point is 168～170 ℃.8.30ppm（CDCl
3/DMSo-d
6）
Example 25
The 3-(4-chlorphenyl)-the 5-(4-trifluoromethyl)-the N-(4-Phenoxyphenyl) pyrazoline-1-Carboxylamide, fusing point is 164～167 ℃.8.00ppm
Example 26
3, two (4-chlorphenyl)-N-(4-(2-fluorophenoxy) phenyl of 5-)-pyrazoline-1-Carboxylamide, fusing point is 174～178 ℃.8.50ppm
Example 27
3, two (4-chlorphenyl)-N-(4-(3-fluorophenoxy) phenyl of 5-)-pyrazoline-1-Carboxylamide, fusing point is 164～168.9.00ppm（DMSo-d
6）
Example 28
3, two (4-chlorphenyl)-N-(4-(4-fluorophenoxy) phenyl of 5-)-pyrazoline-1-Carboxylamide, fusing point is 165～167.9.16ppm（DMSo-d
6）
Example 29
N-(4-(4-chlorophenoxy) phenyl)-3, two (4-the chlorphenyl)-pyrazolines of 5--1-Carboxylamide, fusing point is 142～144 ℃.9.20ppm（DMSo-d
6）
Example 30
3, two (4-chlorphenyl)-N-(4-(4-4-trifluoromethylphenopendant) phenyl of 5-)-pyrazoline-1-Carboxylamide, fusing point is 155～158.8.43ppm（CDCl
3/DMSo-d
6）
Example 31
The 3-(4-chlorphenyl)-N-(4-(4-4-trifluoromethylphenopendant)-phenyl)-the 5-(4-trifluoromethyl) pyrazoline-1-Carboxylamide, fusing point is 144～146 ℃.8.06ppm
Example 32
N-(4-(4-chlorophenoxy) phenyl)-the 5-(4-chlorphenyl)-3-(4-difluoro-methoxy phenyl) pyrazoline-1-Carboxylamide, fusing point is 66～70 ℃.8.60ppm（DMSo-d
6）
Example 33
5-(1,3-benzo dioxole-5-yl)-the 3-(4-chlorphenyl)-the N-(4-Phenoxyphenyl)-pyrazoline-1-Carboxylamide, fusing point is 125～128 ℃.8.36ppm（CDCl
3/DMSo-d
6）
Example 34
5-(1,3-benzo dioxole-5-yl)-N-(4-(4-chlorophenoxy) phenyl)-the 3-(4-chlorphenyl) pyrazoline-1-Carboxylamide, fusing point is 174～175 ℃.8.06ppm
Example 35
N-(2,3-dioxy-2,2-dimethyl benzofuran-5-yl)-3,4-diphenylpyrazoline-1-Carboxylamide, fusing point is 139～143 ℃.7.96ppm
Example 36
3-(4-difluoro-methoxy phenyl)-and N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 72～82 ℃.7.96ppm
Example 37
(±)-3, two (4-the chlorphenyl)-N-(2 of 4-, 3-dihydro-2,2-dimethyl benzofuran-5-yl) pyrazoline-1-Carboxylamide, fusing point is 134～137 ℃.7.93ppm
Example 38
3, two (4-the chlorphenyl)-N-(2 of 5-, 3-dihydro-2,2-dimethyl benzofuran-5-yl) pyrazoline-1-Carboxylamide, fusing point is 175～180 ℃.8.86ppm（DMSo-d
6）
Example 39
N-(1,4-benzodioxan-6-yl)-the 3-(4-chlorphenyl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 112～115 ℃.7.96ppm
Example 40
N-(1,4-benzodioxan-6-yl)-3, two (4-chlorphenyl) pyrazolines of 4--1-Carboxylamide, fusing point is 140～145 ℃.7.96ppm
Example 41
The 3-(4-chlorphenyl)-the N-(4-Phenoxyphenyl)-4-phenylpyrrazolin-1-carbon thioamides, fusing point is 105～110 ℃ of 10.30ppm(DMSo-d
6)
Example 42
3, two (4-the chlorphenyl)-N-(4-Phenoxyphenyls of 4-) pyrazoline-1-carbon thioamides, fusing point is 151～153 ℃ of 9.26ppm(DMSo-d
6)
Example 43
N-(4-(4-chlorophenoxy) phenyl)-3, two (4-the chlorphenyl)-pyrazolines of 4--1-carbon thioamides, fusing point is 179～183 ℃ of 9.10ppm
Example 44
The 3-(4-chlorphenyl)-and N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-4-phenylpyrrazolin-1-carbon thioamides, fusing point is 92～95 ℃ of 10.12ppm(DMSo-d
6)
Example 45
3, two (4-the chlorphenyl)-N-(2 of 4-, 3-dihydro-2,2-dimethyl benzofuran-5-yl) pyrazoline-1-carbon thioamides, fusing point is 149～154 ℃.9.00ppm（DMSo-d
6）
Example 46
N-(1,4-benzodioxan-6-yl) 3, two (4-chlorphenyl) pyrazolines of 5--1-Carboxylamide, fusing point is 83～85 ℃.9.33ppm（DMSo-d
6）
Example 47
The 5-(4-chlorphenyl)-3-(4-fluoroform phenyl)-N-(4-(4-4-trifluoromethylphenopendant) phenyl) pyrazoline-1-Carboxylamide, fusing point is 183～185 ℃.8.77ppm（CDCl
3/DMSo-d
6）
Example 48
N-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-yl)-3-(4-difluoro-methoxy phenyl)-4-phenylpyrrazolin-1-Carboxylamide
1 of propanethiol 33.7 grams (0.13 gram molecule) of the potash of the 2-chloro-4-nitrophenol of 15.0 grams (0.086 gram molecule), 11.9 grams (0.086 gram molecule), 1.5 grams (0.02 gram molecule), the N of 2 dibromotetrafluoroethanes and 115 milliliters, dinethylformamide is placed in the pressure bottle.This pressure bottle is sealed then, and this mixture just is stirred 48 hours under 50 ℃ temperature.Then this pressure bottle is cooled to room temperature, and is opened, and the material in the bottle just is introduced in the separatory funnel.About 200 milliliters 2N(equivalent) sodium hydroxide solution is added in this separatory funnel.Then, extract with four strands 300 milliliters ether mixture again gained.These extracts are merged, and are subjected to two strands of 100 milliliters of 2N(equivalents) the washing of sodium hydroxide solution.To on anhydrous magnesium sulfate, carrying out drying again through the extract that washs and filtering.Then, thus under the condition of decompression, filtered fluid evaporated again and stayed a kind of oil.Reaction described above is repeated again to carry out three times.Residual oil from four experiments is incorporated in together and is cleaned by look partition method in the post on the silica gel, use the normal heptane and the toluene of 95: 5 ratios to carry out elution again, thereby make the solid 3-chloro-4-(2-bromo-1,1 of 57.6 grams, 22-tetrafluoro ethyoxyl) nitrobenzene.
In a pressure bottle, place the 3-chloro-4-(2-bromo-1 of 10.0 grams (0.028 gram molecule), 1,2,2-tetrafluoro ethyoxyl) 2,2 of the copper powder (200 order) of nitrobenzene, 9.0 grams (0.14 gram molecule), 0.45 gram (0.0028 gram molecule) '-dimethyl sulfoxide (DMSO) of bipyridyl and 40 milliliters.Then, this pressure bottle is sealed, and this reactant mixture is just accepted to stir under 190～195 ℃ temperature to reach two hours.Then, this pressure bottle is chilled to room temperature, and after this pressure bottle is opened and pours content into a separatory funnel.About 200 milliliters 2N(equivalent) hydrochloric acid solution is added in this separatory funnel.With three strands 150 milliliters ether this mixture is extracted again.Then, with these extracts and lump together, and then use 200 milliliters of 2N(equivalents) hydrochloric acid solution wash continuously.The extract of process washing is accepted also dry on anhydrous magnesium sulfate and then is accepted filtration.Treat that thereby solution stays a kind of oil after being evaporated under the condition of decompression.Above-described reaction is repeatedly carried out six times again.Residual oil from seven experiments is incorporated in together and purifies by the column chromatography on the silica gel, makes yellow oil thereby carry out elution with toluene.Then, the oil of this yellow is dissolved in 125 milliliters the hexahydrotoluene, and formed solution is placed on and approximately reaches 18 hours in the freezer unit.So crystal has just formed and has been collected after filtration, has so just obtained 2,2,3 of 20.7 grams, 3-tetrafluoro-5-nitrobenzofuran.Thereby filtered fluid is accepted evaporation and is stayed a kind of oil under the condition of decompression.After under the condition of decompression this oil being distilled, just obtained a kind of 3 additional gram products (boiling point be 75 ℃/0.2mmHg)
In 150 milliliters methyl alcohol, get platinum with the oxygen of catalytic amount (0.25 gram) and come 2,2,3 of 2.15 grams (0.011 gram molecule), 3-tetrafluoro-5-nitrobenzene carries out hydrogenation reaction, has so just obtained the 2.15 5-amino-2,2,3 that restrain, 3-tetrafluoro benzofuran.
Be dissolved in the gram of 0.75 in 109 milliliters of toluene (0.0036 gram molecule) 5-amino-2,2,3,3-tetrafluoro benzofuran solution drop by drop joins in the solution that passes through 8.0 milliliter of 20% phosgene (being in the toluene) that stirs.After adding fully, this mixture is just accepted two hours backflow heating.Then, this mixture is cooled off, and solvent just is removed remaining at last residue by the evaporation under reduced pressure.This residue be dissolved in 15 milliliters the ether, and be added into 1.04 gram (0.0036 gram molecule) 3-(4-difluoro-methoxy phenyl through stirring)-solution of 4-phenylpyrrazolin and three triethylamines (being in 100 milliliters of ether) in.After adding fully, this mixture is just accepted one hour backflow heating, is cooled to room temperature then and is subjected to about 18 hours stirring.Remove from this reactant mixture by the evaporation under reduced pressure and to desolvate, stay a kind of solid residue at last.Just obtained 0.99 N-(2 that restrains, 3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-yl by the recrystallization from ethanol)-3-(4-difluoro-methoxy phenyl)-4-phenylpyrrazolin-1-Carboxylamide (fusing point is 155～159 ℃).
Analyze:
Calculated value C:58.58; H:3.29
Measured value C:57.81; H:3.75
Nuclear magnetic resonnance: 8.16ppm
Example 49
3, two (4-the chlorphenyl)-N-(2 of 4-, 2-two fluoro-1,3-benzo dioxole-5-yl) pyrazoline-1-Carboxylamide.
With described method preparation on the document and be dissolved in the gram of 1.18 in 80 milliliters of oxolanes (0.0068 gram molecule) 5-amino-2,2,-two fluoro-1, the solution of 3-benzo dioxole are drop by drop joined in cold (5～10 ℃) solution of 24 milliliter of 20% phosgene (being in the toluene).After adding fully, this mixture is just accepted one hour stirring under 2 ℃ temperature, under the condition of decompression solvent is evaporated and has stayed 1.4 liquid residue that restrain thereby accept 2 hours backflow heating then.
In a clean reaction beaker, this residue of 0.68 gram by joined at leisure through stirring, 0.93 gram (0.0032 gram molecule) 3, in the solution of two (4-chlorphenyl) pyrazolines of 4-and three triethylamines (being in 20 milliliters of ether).After adding fully, this mixture just at room temperature is subjected to about 18 hours stirring.Exist small amount of solid in this reactant mixture, but can remove after filtration and in addition.Under the condition of decompression, this filtered fluid evaporated and stay a kind of residue at last.Come this residue is purified by the column chromatography on the silica gel, and with the normal heptane and the ethyl acetate elution of 1: 1 ratio, thereby 3 of 1.3 grams have been made, two (4-the chlorphenyl)-N-(2 of 4-, 2-two fluoro-1,3-benzo dioxole-5-yl) pyrazoline-1-Carboxylamide, fusing point is 150～155 ℃).
Analyze:
Calculated value C:56.34 H:3.08
Measured value C:57.16 H:2.89
Nuclear magnetic resonnance: 8.10ppm
The compound of example 50 can prepare by similar methods.
Example 50
N-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-3-(4-difluoro-methoxy phenyl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 135～138 ℃.8.10ppm
Example 51
The 3-(4-fluorophenyl)-the N-(4-Phenoxyphenyl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 187～191 ℃.8.10ppm
Example 52
3-(4-difluoro-methoxy phenyl)-the N-(4-Phenoxyphenyl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 139～144 ℃.8.10ppm
Example 53
The 3-(4 chlorphenyl)-N-(4-(4-chlorophenoxy)-phenyl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 170～174 ℃.8.10ppm
Example 54
The 3-(4-chlorphenyl)-N-(4-(4-nitro-phenoxy) phenyl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 187～189 ℃.8.30ppm
Example 55
The 3-(4-chlorphenyl)-N-(4-(4-methoxyl group phenoxy group)-phenyl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 159～160 ℃.8.07ppm
Example 56
The 3-(4-chlorphenyl)-N-(4-(4-difluoromethoxy phenyl oxygen base) phenyl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 181～184 ℃.8.07ppm
Example 57
N-(4-(4-chlorophenoxy) phenyl)-the 3-(4-Trifluoromethoxyphen-l)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 132～134 ℃.8.16ppm
Example 58
N-(4-(4-chlorophenoxy) phenyl)-and 4-phenyl-3-(4-(2-third alkynyloxy group) phenyl) pyrazoline-1-Carboxylamide, fusing point is 160～164 ℃.8.13ppm
Example 59
3-(1,3-benzo dioxole-5-yl)-the N-(4-Phenoxyphenyl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 220～223 ℃.8.06ppm
Example 60
The 4-(4-chlorphenyl)-the N-(4-Phenoxyphenyl)-3-phenylpyrrazolin-1-Carboxylamide, fusing point is 153～155 ℃.8.16ppm
Example 61
3, two (4-the fluorophenyl)-N-(4-Phenoxyphenyls of 4-) pyrazoline-1-Carboxylamide, fusing point is 194～198 ℃.8.16ppm
Example 62
N-(4-(2-chlorophenoxy) phenyl)-3, two (4-chlorphenyl) pyrazolines of 4--1-Carboxylamide, fusing point is 182～186 ℃.8.10ppm
Example 63
3, two (4-chlorphenyl)-N-(the 4-(4-methoxyl group phenoxy group) phenyl of 4-) pyrazoline-1-Carboxylamide.8.20ppm
Example 64
The 3-(4-chlorphenyl)-the 4-(4-fluorophenyl)-the N-(4-Phenoxyphenyl) pyrazoline-1-Carboxylamide, fusing point is 178～179 ℃.8.10ppm
Example 65
N-(4-(4-chlorophenoxy) phenyl)-the 3-(4-chlorphenyl)-the 4-(4-fluorophenyl) pyrazoline-1-Carboxylamide, fusing point is 143～145 ℃.8.03ppm
Example 66
The 3-(4-chlorphenyl)-the 4-(4-aminomethyl phenyl)-the N-(4-Phenoxyphenyl) pyrazoline-1-Carboxylamide, fusing point is 165～168 ℃.8.10ppm
Example 67
N-(4-(4-chlorophenoxy) phenyl)-the 3-(4-chlorphenyl)-the 4-(4-methoxyphenyl) pyrazoline-1-Carboxylamide, fusing point is 169～173 ℃.8.07ppm
Example 68
The 4-(4-fluorophenyl)-the 3-(4-methoxyphenyl)-the N-(4-Phenoxyphenyl) pyrazoline-1-Carboxylamide, fusing point is 184～187 ℃.8.17ppm
Example 69
N-(4-(4-difluoromethoxy phenyl oxygen base) phenyl)-3-(4-difluoro-methoxy phenyl)-the 4-(4-fluorophenyl) pyrazoline-1-Carboxylamide.8.10ppm
Example 70
N-(4-(4-fluorophenoxy) phenyl)-the 3-(4-chlorphenyl)-4-phenylpyrrazolin-1-thiocarboxyl group acid amides, fusing point is 179～183 ℃.9.10ppm
Example 71
3-(4-difluoro-methoxy phenyl)-the N-(4-Phenoxyphenyl)-4-phenylpyrrazolin-1-thiocarboxyl group acid amides, fusing point is 132～136 ℃.9.13ppm
Example 72
The 4-(4-chlorphenyl)-the N-(4-Phenoxyphenyl)-3-phenylpyrrazolin-1-thiocarboxyl group acid amides, fusing point is 131～133 ℃.9.16ppm
Example 73
N-(4-(4-chlorphenyl sulfo-) phenyl)-3,4-diphenylpyrazoline-1-Carboxylamide, fusing point is 186～190 ℃.8.20ppm
Example 74
The 3-(4-chlorphenyl)-N-(4-(4-chlorphenyl sulfo-) phenyl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 178～181 ℃.8.23ppm
Example 75
3-(4-difluoro-methoxy phenyl)-and 4-phenyl-N-(4-phenyl thio-phenyl) pyrazoline-1-Carboxylamide, fusing point is 135～140 ℃.8.13ppm
Example 76
3, two (4-chlorphenyl)-N-(the 4-(4-fluorophenyl sulfo-) phenyl of 4-) pyrazoline-1-Carboxylamide, fusing point is 171～175 ℃.8.20ppm
Example 77
3, two (4-chlorphenyl)-N-(the 4-(4-chlorphenyl sulfo-) phenyl of 4-) pyrazoline-1-Carboxylamide, fusing point is 151～156 ℃.8.13ppm
Example 78
3, two (4-chlorphenyl)-N-(4-(3-chlorophenoxy) phenyl of 4-) pyrazoline-1-Carboxylamide, fusing point is 135～140 ℃.9.20ppm（DMSO-d3）
Example 79
The 3-(4-methoxyphenyl)-the N-(4-Phenoxyphenyl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 188～192 ℃.8.46ppm（CDCl/DMSO-d6）
Example 80
3-(4-(2-third alkynyloxy group) phenyl)-the N-(4-Phenoxyphenyl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 121～126 ℃.8.10ppm
Example 81
The 3-(4-chlorphenyl)-and N-(2,3-Dihydrobenzofuranes-5-yl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 155～158 ℃.7.93ppm
Example 82
3-(4-difluoro-methoxy phenyl)-and N-(2,3-Dihydrobenzofuranes-5-yl)-4-phenylpyrrazolin-1-Carboxylamide.7.93ppm
Example 83
3, two (4-the chlorphenyl)-N-(2 of 4-, 3-Dihydrobenzofuranes-5-yl) pyrazoline-1-Carboxylamide, fusing point is 214～216 ℃.7.93ppm
Example 84
The 3-(4-fluorophenyl)-and N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 156～160 ℃.7.93ppm
Example 85
The 3-(4-methoxyphenyl)-and N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 164～169 ℃.8.00ppm
Example 86
The 3-(4-Trifluoromethoxyphen-l)-and N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 81～83 ℃.7.98ppm
Example 87
N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-4-phenyl-3-(4-(2-third alkynyloxy group) phenyl) pyrazoline-1-Carboxylamide, fusing point is 175～179 ℃.8.00ppm
Example 88
3-(1,3-benzo dioxole-5-yl)-N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 223～227 ℃.8.90ppm（DMSO-d6）
Example 89
The 4-(4-chlorphenyl)-and N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-3-phenylpyrrazolin-1-Carboxylamide.8.00ppm
Example 90
3, two (4-the fluorophenyl)-N-(2 of 4-, 3-dihydro-2,2-dimethyl benzofuran-5-yl) pyrazoline-1-Carboxylamide, fusing point is 161～166 ℃.7.93ppm
Example 91
The 3-(4-chlorphenyl)-the 4-(4-fluorophenyl)-N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl) pyrazoline-1-Carboxylamide, fusing point is 169～171 ℃.7.96ppm
Example 92
The 3-(4-chlorphenyl)-the 4-(4-tolyl)-N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl) pyrazoline-1-Carboxylamide, fusing point is 137～139 ℃.7.96ppm
Example 93
The 3-(4-chlorphenyl)-the 4-(4-methoxyphenyl)-N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl) pyrazoline-1-Carboxylamide, fusing point is 182～186 ℃.7.93ppm
Example 94
The 4-(4-fluorophenyl)-and N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-the 3-(4-methoxyphenyl) pyrazoline-1-Carboxylamide, fusing point is 179～182 ℃.7.93ppm
Example 95
The 4-(4-chlorphenyl)-and N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-the 3-(4-methoxyphenyl) pyrazoline-1-Carboxylamide, fusing point is 157～160 ℃.7.96ppm
Example 96
3-(4-difluoro-methoxy phenyl)-the 4-(4-fluorophenyl)-N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl) pyrazoline-1-Carboxylamide, fusing point is 169～172 ℃.7.93ppm
Example 97
The 4-(4-chlorphenyl)-3-(4-difluoro-methoxy phenyl)-N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl) pyrazoline-1-Carboxylamide, fusing point is 90～95 ℃.7.93ppm
Example 98
3-(4-difluoro-methoxy phenyl)-and N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 152～157 ℃.8.33ppm
Example 99
3-(4-difluoro-methoxy phenyl)-the 4-(4-fluorophenyl)-N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl) pyrazoline-1-Carboxylamide, fusing point is 110～114 ℃.8.33ppm
Example 100
3-(4-difluoro-methoxy phenyl)-the 4-(4-fluorophenyl)-N-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-yl) pyrazoline-1-Carboxylamide, fusing point is 155～159 ℃.8.20ppm
Example 101
The 3-(4-chlorphenyl)-and N-(2,2-dimethyl-1,3-benzo dioxole-5-yl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 182～186 ℃.7.96ppm
Example 102
3-(4-difluoro-methoxy phenyl)-and N-(2,2-dimethyl-1,3-benzo dioxole-5-yl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 148～150 ℃.7.93ppm
Example 103
3, two (4-the chlorphenyl)-N-(2 of 4-, 2-dimethyl-1,3-benzo dioxole-5-yl)-pyrazoline-1-Carboxylamide, fusing point is 168～169 ℃.7.93ppm
Example 104
N-(1,4-benzodioxan-5-yl)-3-(4-difluoro-methoxy phenyl)-4-phenylpyrrazolin-Carboxylamide, 7.93ppm
Example 105
N-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-3-(4-difluoro-methoxy phenyl)-N-methyl-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 110～114 ℃.
Example 106
4-(1,3-benzo dioxole-5-yl)-the N-(4-Phenoxyphenyl)-3-phenylpyrrazolin-1-Carboxylamide, fusing point is 195～197 ℃.8.03ppm
Example 107
The 3-(4-chlorphenyl)-N-4-(4-(1,1-dimethyl ethyl) phenoxy group)-phenyl }-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 192.5～194 ℃.8.03ppm
Example 108
The 3-(4-chlorphenyl)-the 4-(4-fluorophenyl)-N-(4-(4-methylphenoxy) phenyl) pyrazoline-1-Carboxylamide, fusing point is 162～164 ℃.8.03ppm
Example 109
The 3-(4-chlorphenyl)-the 4-(4-fluorophenyl)-N-4-(4-(1,1-dimethyl ethyl) phenoxy group) and phenyl } pyrazoline-1-Carboxylamide, fusing point is 188～198 ℃.8.03ppm
Example 110
The 3-(4-chlorphenyl)-N-4-(4-(1-Methylethyl) phenoxy group) phenyl }-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 181～182.5 ℃.8.06ppm
Example 111
The 3-(4-chlorphenyl)-the 4-(4-fluorophenyl)-N-4-(4-(1-Methylethyl) phenoxy group) and phenyl } pyrazoline-1-Carboxylamide, fusing point is 186～187 ℃.8.06ppm（CDCL3/DMSO-d6）
Example 112
The 3-(4-chlorphenyl)-N-(4-(4-methylphenoxy) phenyl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 150～151 ℃.8.06ppm
Example 113
The 3-(4-chlorphenyl)-N-4-(4-(1-methyl ethoxy) phenoxy group) phenyl }-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 158～160.5 ℃.8.06ppm
Example 114
The 3-(4-chlorphenyl)-the 4-(4-fluorophenyl)-N-4-(4-(1-Methylethyl) phenoxy group) and phenyl } pyrazoline-1-Carboxylamide, fusing point is 182～186 ℃.8.06ppm（CDCL3/DMSO-d6）
Example 115
3, two (4-the fluorophenyl)-N-of 4-4-(4-(1-methyl ethoxy) phenoxy group) and phenyl } pyrazoline-1-Carboxylamide, fusing point is 134～136 ℃.8.06ppm。
Example 116
3, two (4-fluorophenyl)-N-(4-(4-chlorophenoxy) phenyl of 4-) pyrazoline-1-Carboxylamide, fusing point is 197～198.5 ℃.8.70ppm。（CDCL3/DMSO-d6）
Example 117
3, two (4-the fluorophenyl)-N-of 4-4-(4-(1,1-dimethyl ethyl) phenoxy group)-phenyl } pyrazoline-1-Carboxylamide, fusing point is 189～192 ℃.8.70ppm（CDCL3/DMSO-d6）
Example 118
3, two (4-fluorophenyl)-N-N (4-(4-cyano-benzene oxygen) phenyl of 4-) pyrazoline-1-Carboxylamide, fusing point is 198～200 ℃.8.13ppm
Example 119
3, two (4-the fluorophenyl)-N-of 4-4-(4-(N, N-dimethylamino) phenoxy group)-phenyl } pyrazoline-1-Carboxylamide, fusing point is 148～150 ℃.8.02ppm
Example 120
The 3-(4-chlorphenyl)-N-(4-(4-cyano-benzene oxygen) phenyl)-4-phenylpyrrazolin-1-Carboxylamide, fusing point is 170～172 ℃.8.16ppm
Example 121
N-(1,4-benzodioxan-6-yl)-the 4-(4-chlorphenyl)-3-(4-difluoro-methoxy phenyl) pyrazoline-1-Carboxylamide, fusing point is 124～128 ℃.7.93ppm。
Example 122
3, two (4-the chlorphenyl)-N-(2 of 4-, 3-dihydro-2,2-dimethyl benzofuran-5-yl)-N-methylpyrazole quinoline-1-Carboxylamide, fusing point is 150～155 ℃.
Example 123
N-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-3,4-diphenylpyrazoline-1-Carboxylamide, fusing point is 214～216 ℃.8.83ppm（CDCL3/DMSO-d6）
Example 124
N-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-3, two (4-fluorophenyl) pyrazolines of 4--1-Carboxylamide, fusing point is 178～180 ℃.8.10ppm
Example 125
The 3-(4-chlorphenyl)-and N-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-the 4-(4-fluorophenyl) pyrazoline-1-Carboxylamide, fusing point is 147～151 ℃.8.06ppm
Example 126
3-(4-difluoro-methoxy phenyl)-and N-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-yl)-N-methyl-4-phenylpyrrazolin-1-Carboxylamide.
Example 127
The 3-(4-chlorphenyl)-4-(4-difluoro-methoxy phenyl)-N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl) pyrazoline-1-Carboxylamide, fusing point is 150～159 ℃.7.96ppm
Example 128
3-(4-difluoro-methoxy phenyl)-and N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-N-methyl-4-phenylpyrrazolin-1-Carboxylamide.
Example 129
The 4-(4-chlorphenyl)-and N-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-3-(4-difluoro-methoxy phenyl) pyrazoline-1-Carboxylamide.8.06ppm
Example 130
4-(1,3-benzo dioxole-5-yl)-the 3-(4-chlorphenyl)-N-(4-(4-fluorine methoxyl group phenoxy group) phenyl) pyrazoline-1-Carboxylamide.
Example 131
4-(1,3-benzo dioxole-5-yl)-N-(4-(4-chlorophenoxy) phenyl) the 3-(4-chlorphenyl) pyrazoline-1-Carboxylamide.
Example 132
4-(1,3-benzo dioxole-5-yl) the 3-(4-chlorphenyl)-N-(2,2-two fluoro-1,3-benzo dioxole-5-yl) pyrazoline-1-Carboxylamide.
Example 133
4-(1,3-benzo dioxole-5-yl)-the 3-(4-chlorphenyl)-N-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-yl) pyrazoline-1-Carboxylamide.
Example 134
4-(1,3-benzo dioxole-5-yl)-the 3-(4-chlorphenyl)-N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl) pyrazoline-1-Carboxylamide.
Example 135
4-(1,3-benzo dioxole-5-yl)-N-(4-(4-difluoro-methoxy phenyl) phenyl)-3-(4-difluoro-methoxy phenyl) pyrazoline-1-Carboxylamide.
Example 136
4-(1,3-benzo dioxole-5-yl)-N-(4-(4-chlorophenoxy) phenyl)-3-(4-difluoro-methoxy phenyl) pyrazoline-1-Carboxylamide.
Example 137
4-(1,3-benzo dioxole-5-yl)-N-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-3-(4-difluoro-methoxy phenyl) pyrazoline-1-Carboxylamide.
Example 138
4-(1,3-benzo dioxole-5-yl)-3-(4-difluoro-methoxy phenyl)-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-yl) pyrazoline-1-Carboxylamide.
Example 139
4-(1,3-benzo dioxole-5-yl)-3-(4-difluoro-methoxy phenyl)-N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl) pyrazoline-1-Carboxylamide.
Example 140
4-(1,3-benzo dioxole-5-yl)-N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-3-phenylpyrrazolin-1-Carboxylamide.
Example 141
4-(1,3-benzo dioxole-5-yl)-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-yl)-3-phenylpyrrazolin-1-Carboxylamide.
Example 142
4-(1,3-benzo dioxole-5-yl)-N-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-3-phenylpyrrazolin-1-Carboxylamide.
Example 143
4-(1,3-benzo dioxole-5-yl)-N-(4-(4-difluoro-methoxy phenyl) phenyl)-3-phenylpyrrazolin-1-Carboxylamide.
Example 144
4-(1,3-benzo dioxole-5-yl)-N-(4-(4-chlorophenoxy) phenyl)-3-phenylpyrrazolin-1-Carboxylamide.
Example 145
N-(2,2-two fluoro-1,3-benzo dioxole-5-yl) N-(4-(4-difluoro-methoxy phenyl) phenyl)-the 3-(4-chlorphenyl) pyrazoline-1-Carboxylamide.
Example 146
N-(4-(4-chlorphenyl) phenyl)-and 4-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-the 3-(4-chlorphenyl) pyrazoline-1-Carboxylamide.
Example 147
4, two (2,2-two fluoro-1,3-benzo dioxole-5-the yl)-3-(4-fluorophenyls of N-) pyrazoline-1-Carboxylamide.
Example 148
4-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-the 3-(4-fluorophenyl)-N-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-yl) pyrazoline-1-Carboxylamide.
Example 149
4-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-3-(4-fluorophenyl-N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl) pyrazoline-1-Carboxylamide.
Example 150
4-(2-two fluoro-1,3-benzo dioxole-5-yl)-N-(4-(4-difluoro-methoxy phenyl) phenyl)-3-phenylpyrrazolin-1-Carboxylamide.
Example 151
N-(4-(4-difluoro-methoxy phenyl) phenyl)-and 4-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-3-phenylpyrrazolin-1-Carboxylamide.
Example 152
4, two (2,2-two fluoro-1,3-benzo dioxole-5-the yl)-3-phenylpyrrazolin-1-Carboxylamides of N-.
Example 153
4-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-N-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-yl)-3-phenylpyrrazolin-1-Carboxylamide.
Example 154
4-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-N-(2,3-dihydro-2,3-dimethyl benzofuran-5-yl)-3-phenylpyrrazolin-1-Carboxylamide.
Example 155
4-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-N-(4-(4-difluoro-methoxy phenyl) phenyl)-3-(4-difluoro-methoxy phenyl) pyrazoline-1-Carboxylamide.
Example 156
N-(4-(4-difluoro-methoxy phenyl) phenyl)-and 4-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-3-(4-difluoro-methoxy phenyl) pyrazoline-1-Carboxylamide.
Example 157
4, two (2,2-two fluoro-1,3-benzo dioxole-5-the yl)-3-(4-difluoro-methoxy phenyl of N-) pyrazoline-1-Carboxylamide.
Example 158
4-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-3-(4-difluoro-methoxy phenyl) N-(2,3-dihydro-2,2,3, the pyrazoline-1-Carboxylamide of 3-tetrafluoro benzofuran-*-yl).
Example 159
4-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-3-(4-difluoro-methoxy phenyl)-N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl) pyrazoline-1-Carboxylamide.
Example 160
4-(1,4-benzodioxan-6-yl)-the 3-(4-chlorphenyl)-N-(4-(4-difluoromethoxy phenyl oxygen base) phenyl) pyrazoline-1-Carboxylamide.
Example 161
4-(1,4-benzodioxan-6-yl)-N-(4-(4-difluoro-methoxy phenyl) phenyl)-the 3-(4-chlorphenyl) pyrazoline-1-Carboxylamide.
Example 162
4-(1,4-benzodioxan-6-yl)-the 3-(4-chlorphenyl)-N-(2,2-two fluoro-1,3-benzo dioxole-5-yl) pyrazoline-1-Carboxylamide.
Example 163
4-(1,4-benzodioxan-6-yl)-the 3-(4-chlorphenyl)-N-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-yl) pyrazoline-1-Carboxylamide.
Example 164
4-(1,4-benzodioxan-6-yl)-the 3-(4-chlorphenyl)-N-(2,3-two fluoro-2,2-dimethyl benzofuran-5-yl) pyrazoline-1-Carboxylamide.
Example 165
4-(1,4-benzodioxan-6-yl) N-(4-(4-difluoro-methoxy phenyl) phenyl)-3-(4-difluoromethoxy phenyl oxygen base) pyrazoline-1-Carboxylamide.
Example 166
4-(1,4-benzodioxan-6-yl)-N-(4-(4-chlorophenoxy) phenyl)-3-(4-difluoro-methoxy phenyl) pyrazoline-1-Carboxylamide.
Example 167
4-(1,4-benzodioxan-6-yl)-N-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-3-(4-difluoro-methoxy phenyl) pyrazoline-1-Carboxylamide.
Example 168
4-(1,4-benzodioxan-6-yl)-3-(4-difluoro-methoxy phenyl)-N-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-yl) pyrazoline-1-Carboxylamide.
Example 169
4-(1,4-benzodioxan-6-yl)-3-(4-difluoro-methoxy phenyl)-N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl) pyrazoline-1-Carboxylamide.
Example 170
4-(1,4-benzodioxan-6-yl)-N-(4-(4-difluoromethoxy phenyl oxygen base) phenyl)-3-phenylpyrrazolin-1-Carboxylamide.
Example 171
4-(1,4-benzodioxan-6-yl)-N-(4-(4-chlorphenyl) phenyl)-3-phenylpyrrazolin-1-Carboxylamide.
Example 172
4-(1,4-benzodioxan-6-yl)-N-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-3-phenylpyrrazolin-1-Carboxylamide.
Example 173
4-(1,4-benzodioxan-6-yl)-N-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-yl)-3-phenylpyrrazolin-1-Carboxylamide.
Example 174
4-(1,4-benzodioxan-6-yl)-N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-3-phenylpyrrazolin-1-Carboxylamide.
Example 175
3-(1,3-benzo dioxole-5-yl)-N-(4-(4-difluoro-methoxy phenyl) phenyl)-the 4-(4-chlorphenyl)-N-methylpyrazole quinoline-1-Carboxylamide.
Example 176
3-(1,3-benzo dioxole-5-yl)-N-(4-(4-chlorophenoxy) phenyl)-the 4-(4-fluorophenyl) pyrazoline-1-Carboxylamide.
Example 177
3-(1,3-benzo dioxole-5-yl)-N-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-the 4-(4-fluorophenyl) pyrazoline-1-Carboxylamide.
Example 178
3-(1,3-benzo dioxole-5-yl)-the 4-(4-fluorophenyl)-N-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-yl) pyrazoline-1-Carboxylamide.
Example 179
3-(1,3-benzo dioxole-5-yl)-the 4-(4-fluorophenyl)-N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl) pyrazoline-1-Carboxylamide.
Example 180
3-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-N-(4-(4-difluoromethoxy phenyl oxygen base) phenyl)-the 4-(4-fluorophenyl) pyrazoline-1-Carboxylamide.
Example 181
N-(4-4(4-chlorophenoxy) phenyl)-and 3-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-the 4-(4-fluorophenyl)-N-methylpyrazole quinoline-1-Carboxylamide.
Example 182
3, pyrazoline-1-Carboxylamide two (2,2-two fluoro-1,3-benzo dioxole-5-the yl)-4-(4-fluorophenyls of N-).
Example 183
3-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-the 4-(4-fluorophenyl)-N-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-yl) pyrazoline-1-Carboxylamide.
Example 184
3-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-the 4-(4-fluorophenyl)-N-(2,3-dihydro-2,2-dimethyl benzofuran-5 base) pyrazoline-1-Carboxylamide.
Example 185
3-(1,4-benzodioxan-6-yl)-N-(4-(4-difluoro-methoxy phenyl) phenyl)-the 4-phenyl)-pyrazoline-1-Carboxylamide.
Example 186
3-(1,4-benzodioxan-6-yl)-N-(4-(4-chlorophenoxy) phenyl)-the 4-phenyl)-pyrazoline-1-Carboxylamide.
Example 187
3-(1,4-benzodioxan-6-yl)-N-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-N-methyl-4-phenyl) pyrazoline-1-Carboxylamide.
Example 188
3-(1,4-benzodioxan-6-yl)-N-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-yl)-4-pyrazoline-1-Carboxylamide.
Example 189
3-(1,4-benzodioxan-6-yl)-and N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-4-) pyrazoline-1-Carboxylamide.
Example 190
N-(4-(4-difluoromethoxy phenyl oxygen base) phenyl)-and 3-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-the 4-phenyl) pyrazoline-1-Carboxylamide.
Example 191
N-(4-(4-chlorphenyl) phenyl)-and 3-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-4-phenylpyrrazolin-1-Carboxylamide.
Example 192
N-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-3-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-the 4-phenyl) pyrazoline-1-Carboxylamide.
Example 193
N-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-yl)-3-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-N-methyl-4-phenyl) pyrazoline-1-Carboxylamide.
Example 194
3, two (2,3-dihydro-2,2-dimethyl benzofuran-5-the yl)-4-phenyl of N-) pyrazoline-1-Carboxylamide.
Example 195
N-(4-(4-difluoromethoxy phenyl oxygen base) phenyl)-the 4-(4-fluorophenyl)-the 3-(4-aminomethyl phenyl) pyrazoline-1-Carboxylamide.
Example 196
N-(4-(4-chlorphenyl) phenyl)-the 4-(4-fluorophenyl)-the 3-(4-aminomethyl phenyl) pyrazoline-1-Carboxylamide.
Example 197
N-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-the 4-(4-fluorophenyl)-the 3-(4-aminomethyl phenyl) pyrazoline-1-Carboxylamide.
Example 198
The 4-(4-fluorophenyl)-and N-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-base-3-(4-aminomethyl phenyl) pyrazoline-1-Carboxylamide.
Example 199
The 4-(4-fluorophenyl)-and N-(2,3-dihydro-2,2-dimethyl benzofuran-5-base-N-methyl-3-(4-tolyl) pyrazoline-1-Carboxylamide.
Example 200
N-(4-(4-difluoromethoxy phenyl oxygen base) phenyl)-the 4-(3-fluorophenyl)-N-methyl-3-(4-aminomethyl phenyl) pyrazoline-1-Carboxylamide.
Example 201
N-(4-(4-chlorophenoxy) phenyl)-the 4-(3-fluorophenyl)-the 3-(4-tolyl) pyrazoline-1-Carboxylamide.
Example 202
N-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-the 4-(3-fluorophenyl)-the 3-(4-aminomethyl phenyl) pyrazoline-1-Carboxylamide.
Example 203
The 4-(3-fluorophenyl)-and N-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-yl)-the 3-(4-aminomethyl phenyl) pyrazoline-1-Carboxylamide.
Example 204
The 4-(3-fluorophenyl)-and N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-the 3-(4-tolyl) pyrazoline-1-Carboxylamide.
Example 205
N-(4-(4-difluoromethoxy phenyl oxygen base) phenyl)-the 4-(2-fluorophenyl)-the 3-(4-aminomethyl phenyl) pyrazoline-1-Carboxylamide.
Example 206
N-(4-(4-chlorophenoxy) phenyl)-the 4-(3-fluorophenyl)-N-methyl-3-(4-aminomethyl phenyl) pyrazoline-1-Carboxylamide.
Example 207
N-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-the 4-(2-fluorophenyl)-the 3-(4-aminomethyl phenyl) pyrazoline-1-Carboxylamide.
Example 208
The 4-(2-fluorophenyl)-and N-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-yl)-the 3-(4-tolyl) pyrazoline-1-Carboxylamide.
Example 209
The 4-(2-fluorophenyl)-and N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-the 3-(4-aminomethyl phenyl) pyrazoline-1-Carboxylamide.
Example 210
N-(4-(4-difluoromethoxy phenyl oxygen base) phenyl)-the 3-(3-fluorophenyl)-the 4-(4-fluorophenyl) pyrazoline-1-Carboxylamide.
Example 211
N-(4-(4-fluorophenoxy) phenyl)-the 3-(3-fluorophenyl)-the 4-(4-fluorophenyl) pyrazoline-1-Carboxylamide.
Example 212
N-(2,2-two fluoro-1, the assorted amylene of dioxane-5-yl between the 3-benzo)-the 3-(3-fluorophenyl)-the 4-(4-fluorophenyl)-N-methylpyrazole quinoline-1-Carboxylamide.
Example 213
The 3-(3-fluorophenyl)-the 4-(4-fluorophenyl)-N-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-yl) pyrazoline-1-Carboxylamide.
Example 214
The 3-(3-fluorophenyl)-the 4-(4-fluorophenyl)-N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl) pyrazoline-1-Carboxylamide.
Example 215
N-(4-(4-difluoromethoxy phenyl oxygen base) phenyl)-the 3-(2-fluorophenyl)-the 4-(4-fluorophenyl) pyrazoline-1-Carboxylamide.
Example 216
N-(4-(4-chlorophenoxy) phenyl)-the 3-(2-fluorophenyl)-the 4-(4-fluorophenyl) pyrazoline-1-Carboxylamide.
Example 217
N-(2,2-two fluoro-1,3-benzo dioxole-5-yl)-the 3-(2-fluorophenyl)-the 4-(4-fluorophenyl) pyrazoline-1-Carboxylamide.
Example 218
The 3-(2-fluorophenyl)-and the 4-(4-fluorophenyl) N-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-yl)-N-methylpyrazole quinoline-1-Carboxylamide.
Example 219
The 3-(2-fluorophenyl)-the 4-(4-fluorophenyl)-N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl) pyrazoline-1-Carboxylamide.
Example 220
3, two (4-the fluorophenyl)-N-(2 of 4-, 3-dihydro-2,2,3,3,7-phenyl-pentafluoride and furans-5-yl) pyrazoline-1-Carboxylamide.
Example 221
The 4-(4-chlorphenyl)-and N-(2,3-dihydro-2,2,3,3,7-phenyl-pentafluoride and furans-5-yl)-the 3-(4-aminomethyl phenyl) pyrazoline-1-Carboxylamide.
Example 222
N-(2,3-dihydro-2,2,3,3,7-phenyl-pentafluoride and furans-5-yl)-3,4-diphenylpyrazoline-1-Carboxylamide.
Example 223
3-(4-difluoro-methoxy phenyl)-and N-(2,3-dihydro-2,2,3,3,7-phenyl-pentafluoride and furans-5-yl)-4-phenylpyrrazolin-1-Carboxylamide.
Example 224
The 3-(4-chlorphenyl) N-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-yl)-4-phenylpyrrazolin-1-Carboxylamide.
Example 225
3, two (4-the fluorophenyl)-N-(2 of 4-, 2,6-trimethyl-1,3-benzo dioxole-5-yl) pyrazoline-1-Carboxylamide.
Example 226
The 4-(4-chlorphenyl)-and N-(2,2,6-trimethyl-1,3-benzo dioxole-5-yl) pyrazoline-1-Carboxylamide.
Example 227
(2,2,6-trimethyl-1,3-benzo dioxole-5-yl)-3,4-diphenylpyrazoline-1-Carboxylamide.
Example 228
3-(4-difluoro-methoxy phenyl)-and N-(2,2,6-trimethyl-1,3-benzo dioxole-5-yl)-4-phenylpyrrazolin-1-Carboxylamide.
Example 229
The 3-(4-chlorphenyl)-and N-(2,2,6-trimethyl-1,3-benzo dioxole-5-yl)-4-phenylpyrrazolin-1-Carboxylamide.
Example 230
3, two (4-the fluorophenyl)-N-(7-methoxyl groups-2 of 4-, 2-dimethyl-1,3-benzo dioxole 5-yl) pyrazoline-1-Carboxylamide.
Example 231
The 4-(chlorphenyl)-and N-(7-methyl-2,2-1,3-benzo dioxole-5-yl)-the 3-(4-aminomethyl phenyl) pyrazoline-1-Carboxylamide.
Example 232
N-(7-methoxyl group-2,2-dimethyl-1,3-benzo dioxole-5-yl)-3,4-diphenylpyrazoline-1-Carboxylamide.
Example 233
3-(4-difluoro-methoxy phenyl)-and N-(7-methoxyl group-2,2-dimethyl-1,3-benzo dioxole-5-yl)-4-phenylpyrrazolin-1-Carboxylamide.
Example 234
The 3-(4-chlorphenyl)-and N-(7-methoxyl group-2,2-dimethyl-1,3-benzo dioxole-5-yl)-4-phenylpyrrazolin-1-Carboxylamide.
Example 235
3, two (4-the fluorophenyl)-N-(2,2-dimethyl-7-(1-Methylethyl)-1 of 4-, 3-benzo dioxole-5-yl) pyrazoline-1-Carboxylamide.
Example 236
The 4-(4-chlorphenyl)-and N (2,2-dimethyl-7-(1-Methylethyl) 1,3-benzo dioxole-5-yl)-the 3-(4-tolyl) pyrazoline-1-Carboxylamide.
Example 237
N-(2,2-dimethyl-7-(1-Methylethyl) 1,3-benzo dioxole-5-yl)-3,4-diphenylpyrazoline-1-Carboxylamide.
Example 238
3-(4-difluoro-methoxy phenyl)-and N-(2,2-dimethyl-7-(1-Methylethyl) 1,3-benzo dioxole-5-yl)-4-phenylpyrrazolin-1-Carboxylamide.
Example 239
The 3-(4-chlorphenyl)-and N-(2,2-dimethyl-7-(1-Methylethyl) 1,3-benzo dioxole-5-yl)-4-phenylpyrrazolin-1-Carboxylamide.
Example 240
3, two (4-the fluorophenyl)-N-(2 of 4-, 3-dihydro-7-ethyl-2,2,3,3-tetrafluoro benzofuran-5-yl) pyrazoline-1-Carboxylamide.
Example 241
The 4-(4-chlorphenyl)-and N-(2,3-dihydro-7-ethyl-2,2,3,3-tetrafluoro benzofuran-5-yl)-pyrazoline-1-Carboxylamide.
Example 242
N-(2,3-dihydro-7-ethyl-2,2,3,3-tetrafluoro benzofuran-5-yl)-3,4 diphenylpyrazoline-1-Carboxylamide.
Example 243
3-(4-difluoro-methoxy phenyl)-and N-(2,3-dihydro-7-ethyl-2,2,3,3-tetrafluoro benzofuran-5-yl)-4-pyrazoline-1-Carboxylamide.
Example 244
The 3-(4-chlorphenyl)-and N-(2,3-dihydro-7-ethyl-2,2,3,3-tetrafluoro benzofuran-5-yl)-4-phenylpyrrazolin-1-Carboxylamide.
Example 245
The 3-(4-chlorphenyl)-N-(4-(4-sulfonyloxy methyl phenoxyl) phenyl)-4-phenylpyrrazolin-1-Carboxylamide.
Example 246
3, two (4-fluorophenyl)-N-(the 4-(4-sulfonyloxy methyl phenoxyl) phenyl of 4-) pyrazoline-1-Carboxylamide.
Example 247
3-(4-difluoro-methoxy phenyl)-N-(4-(4-sulfonyloxy methyl phenoxyl) phenyl)-4-phenylpyrrazolin-1-Carboxylamide.
Example 248
The 3-(4-chlorphenyl)-the 4-(4-fluorophenyl)-N-(4-(4-sulfonyloxy methyl phenoxyl) phenyl) pyrazoline-1-Carboxylamide.
Example 249
N-(4-(4-sulfonyloxy methyl phenoxyl) phenyl)-3,4-diphenylpyrazoline-1-Carboxylamide.
Example 250
3, two (4-the fluorophenyl)-N-(2 of 4-, 3-dihydro-7-difluoro-methoxy-2,2-dimethyl benzofuran-5-yl) pyrazoline-1-Carboxylamide.
Example 251
The 4-(4-chlorphenyl)-and N-(2,3-dihydro-7-difluoro-methoxy-2,2-dimethyl benzofuran-5-yl)-the 3-(4-aminomethyl phenyl) pyrazoline-1-Carboxylamide.
Example 252
N-(2,3-dihydro-7-difluoro-methoxy-2,2-dimethyl benzofuran-5-yl)-3-diphenylpyrazoline-1-Carboxylamide.
Example 253
3-(4-difluoro-methoxy phenyl)-and N-(2,3-dihydro-7-difluoro-methoxy-2,2-dimethyl benzofuran-5-yl)-4-phenylpyrrazolin-1-Carboxylamide.
Example 254
The 3-(4-chlorphenyl)-and N-(2,3-dihydro-7-difluoro-methoxy-2,2-dimethyl benzofuran-5-yl)-4-phenylpyrrazolin-1-Carboxylamide.
Example 255
N-(7-chloromethyl-2,2-dimethyl-1,3-benzo dioxole-5-yl) 3, two (4-fluorophenyl) pyrazolines of 4--1-Carboxylamide.
Example 256
N-(7-chloromethyl-2,2-dimethyl-1,3-benzo dioxole-5-yl)-the 4-(4-chlorphenyl)-the 3-(4-aminomethyl phenyl) pyrazoline-1-Carboxylamide.
Example 257
N-(7-chloromethyl-2,2-dimethyl-1,3-benzo dioxole-5-yl)-3,4-diphenylpyrazoline-1-Carboxylamide.
Example 258
N-(7-chloromethyl-2,2-dimethyl-1,3-benzo dioxole-5-yl) 3-(4-difluoro-methoxy phenyl)-4-phenylpyrrazolin-1-Carboxylamide.
Example 259
N-(7-chloromethyl-2,2-dimethyl-1,3-benzo dioxole-5-yl)-the 3-(4-chlorphenyl)-4-phenylpyrrazolin-1-Carboxylamide.
Example 260
N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-3-(7-(1-Methylethyl)-2,2-dimethyl-1,3-benzo dioxole-5-yl)-4-phenylpyrrazolin-1-Carboxylamide.
Example 261
N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-3-(7-methoxyl group-2,2-dimethyl-1,3-benzo dioxole-5-yl)-4-phenylpyrrazolin-1-Carboxylamide.
Example 262
N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-3-(7-fluorine 2,2-dimethyl-1,3-benzo dioxole-5-yl)-4-phenylpyrrazolin-1-Carboxylamide.
Example 263
N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-3-(7-difluoro-methoxy-2,2-dimethyl-1,3-benzo dioxole-5-yl)-4-phenylpyrrazolin-1-Carboxylamide.
Example 264
N(2,2-two fluoro-1,3-benzo dioxole-5-yl) the 3-(4-fluorophenyl)-4-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl) pyrazoline-1-Carboxylamide.
Example 265
N-(2,2-two fluoro-1,3-benzo dioxole-5-yl) the 3-(4-fluorophenyl)-4-N-(2,3-dihydro-2,2,3,3-tetrafluoro benzofuran-5-yl) pyrazoline-1-Carboxylamide.
Example 266
N-(3-(4-4-trifluoromethylphenopendant) phenyl) 3, two (4-fluorophenyl) pyrazolines of 4--1-Carboxylamide.
Example 267
N-(3-(4-fluorophenoxy) phenyl) 3, two (4-fluorophenyl) pyrazolines of 4--1-Carboxylamide.
Example 268
N-(3-(4-difluoromethoxy phenyl oxygen base) phenyl)-3, two (4-fluorophenyl) pyrazolines of 4--1-Carboxylamide.
Example 269
3, two (4-fluorophenyl)-N-(3-(4-methylphenoxy) phenyl of 4-) pyrazoline-1-Carboxylamide.
Example 270
3-(7-chloromethyl-2,2-dimethyl-1,3-benzo dioxole-5-yl)-4, two (4-fluorophenyl) pyrazolines of N--1-Carboxylamide.
Example 271
N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-4-(7-(1-Methylethyl)-2,2-dimethyl-1,3-benzo dioxole-5-yl)-3-phenylpyrrazolin-1-Carboxylamide.
Example 272
N-(2,3-dihydro-2,2 ,-dimethyl benzofuran-5-yl)-4-(-7 methoxyl group-2,2-dimethyl-1,3-benzo dioxole-5-yl)-3-phenylpyrrazolin-1-Carboxylamide.
Example 273
N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-4(7-two fluoro-2,2-dimethyl-1,3-benzo dioxole-5-yl)-3-phenylpyrrazolin-1-Carboxylamide.
Example 274
N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-4-(7-difluoro-methoxy-2,2-dimethyl-1,3-benzo dioxole-5-yl)-3-phenylpyrrazolin-1-Carboxylamide.
Example 275
4-(7-chloromethyl-2,2-dimethyl-1,3-benzo dioxole-5-yl)-3, two (4-fluorophenyl) pyrazolines of N--1-Carboxylamide.
Usually in the process that desinsection pyrazoline of the present invention is used, these pyrazolines generally are used nothing more than the state with admixture or dilution, but usually be to be used in the composition that suitable that make by prescription and an application method adapt, and the amount of the pyrazoline that this composition contained reach insecticidal effect.The same with most of insecticides tested, the carrier fusion mutually that pyrazoline of the present invention can be gone up acceptable surfactant and be commonly used to impel active constituent to disperse with those agriculturals, this is that promptly a kind of composition of insecticide and occupation mode thereof will influence the activity of this material because we have seen so putative fact.The pyrazoline of the present invention for example form of spray liquid, pulvis or granule is applied to the place that need prevent and treat insect, and the mode of using yes according to the difference of insect and environment and difference.So pyrazoline of the present invention can be made into pulvis, the wetting powder of bulky grain agent, powdery, emulsible concentrate (missible oil) and solution or the like by prescription.
Granule can comprise particle porous or non-porous, for example Attagel (attapulgite) or sand, these atlapulgites or the husky carrier that for example can be used as pyrazoline.This granule particle is bigger, and its diameter typically is approximately 400～2500 microns.These particles or be immersed in the pyrazoline of solution shape or with pyrazoline apply, and then use stickum sometimes.Granule normally contains 0.05～10% the active constituent amount as desinsection validity, but preferably 0.5～5%.
Pulvis is the mixture of pyrazoline and diffusing solid in small, broken bits, and these solids have talcum powder, Attagel, diatomite (kieselguhr), pyrophyllite, talcum powder, diatomite (diato maccous carth), calcium phosphate, calcium carbonate and magnesium carbonate, sulphur, flour and other can be as the organic or inorganic solid of insecticide carrier.
These its average particle sizes of diffusing solid in small, broken bits are less than about 50 microns.One wp formula that typically is used for effective pest control contains a pyrazoline.3-(4-chlorphenyl for example)-N-(4-(4-chlorophenoxy) phenyl)-4-phenylpyrrazolin-1-Carboxylamide and contain 99 parts of talcum powder.
Pyrazoline of the present invention can or be emulsified in the suitable liquid and be made into liquid concentrate by dissolving, also can carry out fusion and makes solid concentrates by being used in known solid state carrier in the insecticide technical field with talcum powder, carclazyte and other.This concentrate is some mixtures, wherein contain about 5～50% pyrazoline as the insecticide effective dose, 3-(4-chlorphenyl for example)-N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-4-phenylpyrrazolin-1-Carboxylamide, also contain 95～50% inert substance, these inert substances, comprise surface-active dispersant, emulsifier and wetting agent, yet, the higher concentration of active constituent also can be used experimentally.Concentrate by water or other by practical application be spray liquid liquid diluted, or the solid-state carrier that adds that is used as pulvis dilutes.
The typical carrier that is applicable to solid-state concentrate (also being known as wetting powder) comprise Emathlite (bleaching earth) (fulier searth) carclazyte, silica and other have high-absorbable can, moistening inorganic diluents easily.A kind of solid-state concentrate prescription that is used for effective pest control contains as the sodium lignin sulfonate of wetting agent and each 3-(4-chlorphenyl of 1.5 parts, 25 parts of lauryl sodium sulfate)-N-(2,3-dihydro-2,2-dimethyl benzofuran-5-yl)-and the 4-(4-chlorphenyl) Attagel of phenylpyrrazolin-1-Carboxylamide and 72 parts.
Making concentrate will help low melting point product of the present invention is transported by sea.This concentrate prepares by following approach, promptly the low melting point solid product is dissolved in the above solvent of one of one of percentage or percentage, thereby obtains a kind of in the freezing point that is cooled to clean product or more do not produce the concentrate of curing during low temperature.
Useful liquefied concentrate comprises emulsible concentrate.They are the liquid of homogeneous phase or are dispersed in the water easily or the pasty mixture in other liquid carriers.They can be made up of the pyrazoline of liquid or solid emulsifier band fully or they also can contain liquid carrier, for example dimethylbenzene, heavy aromatic series naphtha, isophorone and other more not volatile organic solvents.On using, these concentrates are dispersed in the water or in other liquid carriers, are applied to the place that need administer and normally be used as spray liquid.
Typical surface-active wetting agent, dispersant and the emulsifier of use in insecticidal formulation comprise, for example alkyl and alkylaryl sulfonate and sulphate and their sodium salt, and alkylamide sulfonate comprises fatty N-methyltaurine class; The alkyl aryl polyether alcohol class, Sulfated higher alcohols, polyvinyl alcohol, PEO, the animal oil of sulfonation and vegetable oil; The oil of phosphatization; The oxirane additive product of the fatty acid ester of polyalcohol and this class ester; And the addition compound product of long-chain mercaptan and oxirane.The useful surfactant of many other types can have been bought on market.This surfactant contains 1～15%(weight of having an appointment in use usually) the insecticide composition.
Other useful prescriptions comprise that active constituent is in the simple solution in the solvent, and active constituent is completely soluble in this solvent, thereby can provide required concentration, and described this kind solvent has for example acetone or other organic solvents.
In insecticidal compositions (for application diluted), the pyrazoline of amount with insecticidal effect is normally in about 0.001%～8%(weight) scope in.The insecticidal compositions known in the art agent many kinds of versions that spread that loose of spraying and levigate can be utilized by such approach, promptly pyrazoline of the present invention be replaced to known in the art or obvious component.
Insecticide of the present invention batching can with other active constituent preparation, these active constituents comprise other insecticide, nematocide, miticide, fungicide, plant growth regulator, fertilizer or the like.When using this mixture to come pest control, the pyrazoline that only need will have the amount of insecticidal effect is administered to the place that need prevent and treat and gets final product.Perhaps, this place is for example edible plant of insect itself, insect or the habitat of insect.When this place is soil, for example be the soil that crops have been planted or will have been planted, at this moment, this active compound just can be applied in soil or randomly be incorporated in the soil and go.Concerning majority was used, a kind of amount with insecticidal effect was about per hectare 75～4000 grams, but preferably 150～3000 restrains.
The biocidal activity of the pyrazolines that its preparation process is described is in the above estimated as follows:
In foliage application, this compound has been done test with various concentration in the aqueous solution that contains 10% acetone and 0.25% many ethyoxyls of Octylphenoxy acetaldehyde.Pinto class plant is placed in the interior turntable that is rotating of protective cover, and then, this testing liquid is just by an atomizers spray.This testing liquid is injected on the surface of the upper and lower of plant leaf and just drips subsequently.This plant carries out dry and is cut off by the root at stem with regard to allowing then.Every rhizome is inserted in the water by a dixie cup.The insect of ten suitable kinds is placed in each cup, and cup is built.Southern mythimna separata (Spodoptera eridania), Mexico soybean beetle (Epilachna varivestis), beet mythimna separata (Spodopteraexigua) and cabbage looper (Trichoplusia nia) have been used during mensuration.After four days, lethality just is read out under 26 ℃ and 50% relative temperature.If the test value that the results are shown in the table 1 of test is read more early, insect mortality is generally just less so.
Also be effectively to preventing and treating the larva (Diabrot undecimpunctata howardi Barber) of boring the moth corn root in south when some pyrazolines are applied in the soil, those underproof pyrazolines also are effectively to the beetle (Leptinotara dece-mlineata Say) of control Colorado potato.
The table I
The evaluation of foliage application
Chemical combination material consumption medicine rate
Insect %(kills)
（PPM） M＊＊ SAW BAM CL
1 500 100 100
2 500 100 100
3 500 100 100
4 500 100 100
5 250 100 87 100
6 500 70 68 90
7 500 100 50 90
8 500 100 85
9 500 90 70
10 500 100 35
11 500 85 15
12 500 100 100
13 500 93 50
14 500 100 100
15 500 100 90
16 500 100
17 500 100 35
18 500 90 55
19 500 100 100
20 500 80 40
21 500 70 15
22 500 100 100
23 500 40 30
24 250 95
25 500 30 75
26 500 80 65
27 500 75 95
28 500 95 90
29 500 10 90
30 500 5 64
31 500 5 65 70
32 500 100 50
33 500 100 80
34 500 10 75
35 500 100 100
36 8 100 98 45 90
37 32 98 98 97 100
38 500 95 80
39 500 100 25
40 500 100 100
41 128 95 70
42 128 95 100
43 500 100 100
44 500 100 100
45 32 100 100 100 100
46 500 30 40
47 500 5 10
48 8 100 100 100 95
49 500 100 100
50 500 100 100
51 100 40 60
52 500 100 95
53 500 100 10
54 500 100 85
55 500 100 80
56 500 100 100
57 250 100 100
58 500 100 40
59 500 100 100
60 200 100 60
61 32 54 100 55 90
62 500 95 95
63 500 100 95
64 500 100 100
500 100 100
66 500 100 100
67 500 85 95
68 500 100 0
69 8 100 60 5 100
70 500 100 100
71 200 60 10
72 200 100 30
73 500 100 90
74 500 100 80
75 200 100 45
76 200 95 100
77 500 80
200 0 95
78 500 90 55
79 200 95 60
80 500 100 100
81 250 100 100
82 128 100 90
83 250 85 100
84 100 100 90
85 200 100 100
86 16 95 95 40 100
87 500 100 100
88 100 100 25 40 85
89 200 100 100
90 16 100 100 100 90
91 32 100 100 100 100
92 500 100 100
93 500 100 100
94 500 100 100
95 200 100 90
96 32 100 100 85 95
97 8 100 100 85
98 16 100 40 35 80
99 16 100 100 90 85
100 32 100 100 100 100
101 1000 100 100
102 128 100 100
103 16 90 95 15 100
104 16 100 100
105 256 100 70
106 1000 45 0
107 1000 100 75
108 1000 0 0
109 1000 70 0
110 1000 0 0
111 1000 100 90
112 1000 100 10
113 1000 100 30
114 1000 100 15
115 500 100 100
116 500 55 0
117 500 100 100
118 500 100 95
119 500 100 100
120 500 95 100
121 64 100 100
122 64 15 0
123 64 100 100
124 64 100 100
MBB=Mexico soybean beetle
SAW=south mythimna separata
BAW=beet mythimna separata
CL=cabbage looper
Claims (50)
1, a kind of insecticidal compositions is made up of acceptable carrier on the agricultural and insecticidal activity component, it is characterized in that agriculture upward acceptable carrier is in a liquid state or is solid-state, its content is 5-99.99%, and the content of insecticidal activity component is 0.01-95%, and said insecticidal activity component is that chemical formula is
The desinsection pyrazoline, in this chemical formula, the chemical formula of R is
R ' wherein is select from hydrogen, halogen, low alkyl group, lower alkoxy, rudimentary halogen alkoxyl, rudimentary alkynyloxy group and rudimentary alkylhalide group, or
X in the base be chemical formula be (O-(CR '
AAR '
AB)
a-O
a') bridge connector, a here is 1～3, a ' is 0 or 1, a+a ' is at least 2 but be not more than 3, R '
AAAnd R '
ABBe at random select from hydrogen, halogen and low alkyl group, and R '
ACBe select from hydrogen, halogen, low alkyl group, lower alkoxy, rudimentary halogen alkoxyl and rudimentary alkylhalide group, the R in this desinsection pyrazoline chemical formula
BBe that chemical formula is
4-or-substituting group, R ' wherein is select from hydrogen, halogen, low alkyl group, lower alkoxy and rudimentary alkylhalide group, or
Y wherein be chemical formula be (O-(CR '
BAR '
BB) b-Ob ') bridge connector, the b here is 1～3, and b ' is 0 or 1, and b+b ' is at least 2 but be not more than 3, R '
BAAnd R '
BBBe at random select from hydrogen, halogen and low alkyl group, and R '
BCBe select from hydrogen, halogen, low alkyl group, lower alkoxy, rudimentary halogen alkoxyl and rudimentary alkylhalide group; R in this desinsection pyrazoline chemical formula
cIts chemical formula is
R wherein
DBe select from hydrogen and low alkyl group; R
EBe from halogen low alkyl group, lower alkoxy, rudimentary halogen alkoxyl, rudimentary alkylhalide group, cyano group, nitro ,-NR
FR
G(the R here
FAnd R
GBe low alkyl group arbitrarily) and SO
nR
H(the R here
HBe low alkyl group and n is 0～2) in select; Or
Z wherein be chemical formula be (O-(CR '
CAR '
CB)
c-O
c') bridge connector, the c here is 1～3, c ' is 0 or 1, c+c ' is at least 2 but be not more than 3, R '
CAAnd R '
CBBe at random select from hydrogen, halogen and low alkyl group, but precondition be when c be 1 and c ' when being 1, R '
CAAnd R '
CBThe two can not all be hydrogen and R '
CcBe select from hydrogen, halogen, low alkyl group, lower alkoxy, rudimentary halogen alkoxyl and rudimentary alkylhalide group; R in this desinsection pyrazoline chemical formula
NBe hydrogen or low alkyl group, and V and W are oxygen or sulphur arbitrarily.
2, mixture as claimed in claim 1, it is characterized by W is oxygen.
3, mixture as claimed in claim 1 is characterized by R '
ABe halogen or rudimentary halogen alkoxyl.
4, mixture as claimed in claim 1 is characterized by R
BIt is the 4-substituting group.
5, a kind of method of pest control, it is characterized in that the mixture that contains the desinsection pyrazoline of insecticidal effect amount is administered to the place that need carry out pest control by foliage application or soil pesticide, or directly be sprayed onto on the insect, said desinsection pyrazoline is to be from chemical formula
Compound, R in this pyrazoline chemical formula
AChemical formula be
R ' wherein
ABe select from hydrogen, halogen, low alkyl group, lower alkoxy, rudimentary halogen alkoxyl, rudimentary alkynyloxy group and rudimentary alkylhalide group; Or
X wherein be chemical formula be (O-(CR '
ABR '
AB) a-Oa ') and bridge connector, a here is 1～3, a ' is 0 or 1, a+a ' is at least 2 but be not more than 3, R '
AAAnd R '
ABBe select from hydrogen, halogen and low alkyl group arbitrarily, and R '
ACBe select from hydrogen, halogen, low alkyl group, lower alkoxy, rudimentary halogen alkoxyl and rudimentary alkylhalide group, the R in this pyrazoline chemical formula
BBe that chemical formula is
4-or 5-substituting group, R ' wherein
BBe select from hydrogen, halogen, low alkyl group, lower alkoxy and rudimentary alkylhalide group, or
Y wherein be chemical formula be (O-(CR '
BAR '
BB) b-Ob ') and bridge connector, the b here is 1～3, b ' is 0 or 1, b+b ' is at least 2 but be not more than 3, R '
BAAnd R '
BBBe at random select from hydrogen, halogen and low alkyl group, lower alkoxy, rudimentary halogen alkoxyl and rudimentary alkylhalide group, the R in this pyrazoline chemical formula
CChemical formula be
R wherein
DBe select from hydrogen and low alkyl group; R
EBe from low alkyl group, halogen, lower alkoxy, rudimentary halogen alkoxyl and rudimentary alkylhalide group, cyano group, nitro ,-NR
FR
G(the R here
FAnd R
GBe low alkyl group arbitrarily) and-SO
nR
H(the R here
HBe low alkyl group, and n is 0～2) in select, or
Z wherein be chemical formula be (O-(CR '
CAR '
CB)
c-O
c') bridge connector, the c here is 1～3, c ' is 0 or 1, c+c ' is at least 2 but be not more than 3, R '
CAAnd R '
CBBe at random select from hydrogen, halogen and low alkyl group, but precondition be when c be 1 and c ' R ' when being 1
CAAnd R '
CBThe two can not all be a hydrogen, and R '
CCBe select from hydrogen, halogen, low alkyl group, lower alkoxy, rudimentary halogen alkoxyl and rudimentary alkylhalide group, the R in this desinsection pyrazoline chemical formula
NBe hydrogen or low alkyl group, and V and W are oxygen or sulphur arbitrarily.
6, mixture as claimed in claim 1 is characterized in that its insecticidal active ingredient pyrazoline manufacture method is that to make chemical formula be R
cThe compound of-N=C=W and chemical formula are
Compound react, thereby and at random product is implemented alkylation and makes chemical formula and be
The desinsection pyrazoline, here, R
AChemical formula be
R ' wherein
ABe select from hydrogen, halogen, low alkyl group, lower alkoxy, rudimentary halogen alkoxyl, rudimentary alkynyloxy group and rudimentary alkylhalide group, or
X wherein be chemical formula be (O-(CR '
AAR '
AB) a-Oa ') and bridge connector, a here is 1～3, a ' is 0 or 1, a+a ' is at least 2 but be not more than 3, R '
AAAnd R '
ABBe at random select from hydrogen, halogen and low alkyl group, and R '
AOBe select from hydrogen, halogen, low alkyl group, lower alkoxy, rudimentary halogen alkoxyl and rudimentary alkylhalide group, the R in this desinsection pyrazoline chemical formula
BBe that chemical formula is
4-or 5-substituting group, R ' wherein
BBe select from hydrogen, halogen, low alkyl group, lower alkoxy and rudimentary alkylhalide group, or
Y wherein be chemical formula be (O-(CR '
BAR '
BB) b-Ob ') and bridge connector, the b here is 1～3, b ' is 0 or 1, b+b ' is at least 2 but be not more than 3, R '
BAAnd R '
BBBe arbitrarily select from hydrogen, halogen and low alkyl group, and R '
BCBe select from hydrogen, halogen, low alkyl group, lower alkoxy, rudimentary halogen alkoxyl and rudimentary alkylhalide group, the R in this desinsection pyrazoline chemical formula
cChemical formula be
R wherein
DBe select from hydrogen and low alkyl group, R
EBe from low alkyl group, halogen, lower alkoxy, rudimentary halogen alkoxyl, rudimentary alkylhalide group, cyano group, nitro, NR
FR
G(the R here
FAnd R
GBe low alkyl group arbitrarily) and SO
nR
H(the R here
HBe low alkyl group and n is 0～2) in select, or
Z wherein be chemical formula be (O-(CR '
CAR '
CA) c-O
c') bridge connector, the c here is 1～*, c ' is 0 or 1, c+c ' is at least 2 but be not more than 3, R '
CAAnd R '
CBBe at random select from hydrogen, halogen and low alkyl group, but precondition be when c be 1 and c ' when being 1, R '
CAAnd R '
CBAnd not all be hydrogen, and R '
CcBe select from hydrogen, halogen, low alkyl group, lower alkoxy, rudimentary halogen alkoxyl and rudimentary alkylhalide group, the R in this desinsection pyrazoline chemical formula
NBe hydrogen or low alkyl group, and V and W are oxygen or sulphur arbitrarily.
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66467484A | 1984-10-25 | 1984-10-25 | |
| US664,674 | 1984-10-25 | ||
| US70962685A | 1985-03-08 | 1985-03-08 | |
| US709,626 | 1985-03-08 | ||
| US77972185A | 1985-09-24 | 1985-09-24 | |
| US779,721 | 1985-09-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN85107882A CN85107882A (en) | 1986-06-10 |
| CN1004272B true CN1004272B (en) | 1989-05-24 |
Family
ID=27418114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN85107882.6A Expired CN1004272B (en) | 1984-10-25 | 1985-10-24 | Pyrazoline insecticides |
Country Status (30)
| Country | Link |
|---|---|
| KR (1) | KR880001568B1 (en) |
| CN (1) | CN1004272B (en) |
| AP (1) | AP36A (en) |
| AT (1) | ATA306085A (en) |
| AU (1) | AU556949B2 (en) |
| BE (1) | BE903521A (en) |
| BR (1) | BR8505326A (en) |
| CA (1) | CA1265145A (en) |
| CH (1) | CH666029A5 (en) |
| CS (1) | CS252497B2 (en) |
| DE (1) | DE3537884A1 (en) |
| DK (1) | DK487885A (en) |
| EG (1) | EG17848A (en) |
| ES (1) | ES8701757A1 (en) |
| FR (1) | FR2572400A1 (en) |
| GB (1) | GB2166137B (en) |
| GR (1) | GR852585B (en) |
| HU (1) | HU199808B (en) |
| IL (1) | IL76771A0 (en) |
| IN (1) | IN166473B (en) |
| IT (1) | IT1203596B (en) |
| LU (1) | LU86134A1 (en) |
| MY (1) | MY102602A (en) |
| NL (1) | NL8502913A (en) |
| NZ (1) | NZ213953A (en) |
| OA (1) | OA08127A (en) |
| PL (1) | PL150265B1 (en) |
| RO (1) | RO92966B (en) |
| SE (1) | SE8505026L (en) |
| YU (1) | YU45287B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3545786A1 (en) * | 1985-12-21 | 1987-06-25 | Schering Ag | Pyrazoline derivatives, their preparation, and their use as insecticides |
| EP0367796A1 (en) * | 1987-07-17 | 1990-05-16 | E.I. Du Pont De Nemours And Company | Insecticidal pyrazolines |
| ZW9688A1 (en) * | 1987-07-17 | 1989-04-12 | Du Pont | Insecticidal pyrazolines |
| JPH04501108A (en) * | 1988-09-22 | 1992-02-27 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | Substituted indazole arthropodicides |
| JPH05112556A (en) * | 1991-10-18 | 1993-05-07 | Nippon Bayeragrochem Kk | Insecticidal pyrazolines |
| US5684041A (en) * | 1996-02-01 | 1997-11-04 | The Procter & Gamble Company | Dihydrobenzofuran and related compounds useful as anti-inflammatory agents |
| CN116265457B (en) * | 2021-12-17 | 2024-09-03 | 湖南化工研究院有限公司 | N-oxa condensed ring amide compound and preparation method and application thereof |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE795264A (en) * | 1972-02-09 | 1973-08-09 | Philips Nv | NEW PYRAZOLINE COMPOUNDS WITH INSECTICIDAL ACTIVITY |
| NL158178B (en) * | 1974-07-12 | 1978-10-16 | Philips Nv | METHOD OF PREPARING INSECTICIDE PREPARATIONS CONTAINING A PYRAZOLINE DERIVATIVE, SO PREPARED PREPARATIONS, AND METHOD OF PREPARING PYRAZOLINE DERIVATIVES WITH INSECTICIDE ACTION. |
| US4174393A (en) * | 1975-07-09 | 1979-11-13 | Duphar International Research B.V. | 1,3,4-Substituted pyrazoline derivatives |
| NL183400C (en) * | 1976-01-09 | 1988-10-17 | Duphar Int Res | METHOD FOR PREPARING AN INSECTICIDE PREPARATION CONTAINING A PYRAZOLINE COMPOUND AND METHOD FOR PREPARING A PYRAZOLINE COMPOUND WITH INSECTICIDE ACTION |
| ATE4593T1 (en) * | 1979-07-03 | 1983-09-15 | Duphar International Research B.V | PYRAZOLINE DERIVATIVES, PROCESSES FOR THE PREPARATION OF THESE COMPOUNDS, AND INSECTICIDE COMPOSITION BASED ON THESE COMPOUNDS. |
| GB2093836B (en) * | 1981-02-17 | 1984-09-05 | Nissan Chemical Ind Ltd | Insecticidal pyrazoline derivatives |
| US4407813A (en) * | 1981-02-17 | 1983-10-04 | Nissan Chemical Industries Ltd. | Insecticidal pyrazoline derivatives and composition |
| DE3376212D1 (en) * | 1982-12-30 | 1988-05-11 | Schering Agrochemicals Ltd | PYRAZOLINE INSECTICIDES |
-
1985
- 1985-10-15 AU AU48598/85A patent/AU556949B2/en not_active Ceased
- 1985-10-16 IN IN864/DEL/85A patent/IN166473B/en unknown
- 1985-10-16 CA CA000493018A patent/CA1265145A/en not_active Expired - Lifetime
- 1985-10-21 IL IL76771A patent/IL76771A0/en not_active IP Right Cessation
- 1985-10-23 LU LU86134A patent/LU86134A1/en unknown
- 1985-10-23 GB GB08526175A patent/GB2166137B/en not_active Expired
- 1985-10-23 AP APAP/P/1985/000014A patent/AP36A/en active
- 1985-10-23 AT AT0306085A patent/ATA306085A/en not_active Application Discontinuation
- 1985-10-24 CN CN85107882.6A patent/CN1004272B/en not_active Expired
- 1985-10-24 BR BR8505326A patent/BR8505326A/en unknown
- 1985-10-24 SE SE8505026A patent/SE8505026L/en not_active Application Discontinuation
- 1985-10-24 DK DK487885A patent/DK487885A/en not_active Application Discontinuation
- 1985-10-24 KR KR1019850007838A patent/KR880001568B1/en not_active IP Right Cessation
- 1985-10-24 HU HU854103A patent/HU199808B/en unknown
- 1985-10-24 ES ES548170A patent/ES8701757A1/en not_active Expired
- 1985-10-24 CS CS857615A patent/CS252497B2/en unknown
- 1985-10-24 NZ NZ213953A patent/NZ213953A/en unknown
- 1985-10-24 NL NL8502913A patent/NL8502913A/en not_active Application Discontinuation
- 1985-10-24 CH CH4582/85A patent/CH666029A5/en not_active IP Right Cessation
- 1985-10-24 IT IT22601/85A patent/IT1203596B/en active
- 1985-10-24 DE DE19853537884 patent/DE3537884A1/en not_active Ceased
- 1985-10-24 YU YU1686/85A patent/YU45287B/en unknown
- 1985-10-25 FR FR8515890A patent/FR2572400A1/en not_active Withdrawn
- 1985-10-25 RO RO120544A patent/RO92966B/en unknown
- 1985-10-25 GR GR852585A patent/GR852585B/el unknown
- 1985-10-25 PL PL1985255938A patent/PL150265B1/en unknown
- 1985-10-25 BE BE0/215778A patent/BE903521A/en not_active IP Right Cessation
- 1985-10-25 OA OA58712A patent/OA08127A/en unknown
- 1985-10-27 EG EG680/85A patent/EG17848A/en active
-
1987
- 1987-09-29 MY MYPI87002197A patent/MY102602A/en unknown
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