HU199808B - Process for producing pyrazoline derivatives and insecticides comprising pyrazoline derivatives as active ingredient - Google Patents
Process for producing pyrazoline derivatives and insecticides comprising pyrazoline derivatives as active ingredient Download PDFInfo
- Publication number
- HU199808B HU199808B HU854103A HU410385A HU199808B HU 199808 B HU199808 B HU 199808B HU 854103 A HU854103 A HU 854103A HU 410385 A HU410385 A HU 410385A HU 199808 B HU199808 B HU 199808B
- Authority
- HU
- Hungary
- Prior art keywords
- phenyl
- carboxamide
- pyrazoline
- priority
- dihydro
- Prior art date
Links
- 150000003219 pyrazolines Chemical class 0.000 title claims description 33
- 239000004480 active ingredient Substances 0.000 title claims description 31
- 238000000034 method Methods 0.000 title claims description 15
- 239000002917 insecticide Substances 0.000 title description 9
- -1 1,3-benzodioxol-5-yl Chemical group 0.000 claims description 92
- 239000000203 mixture Substances 0.000 claims description 49
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 46
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 230000000749 insecticidal effect Effects 0.000 claims description 34
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
- IJHUAFAXEQBNHG-UHFFFAOYSA-N N-(4-fluorophenyl)-1,3-dihydropyrazole-2-carboxamide Chemical compound N1(NC=CC1)C(=O)NC1=CC=C(C=C1)F IJHUAFAXEQBNHG-UHFFFAOYSA-N 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- PPVUWDCETZMPLT-UHFFFAOYSA-N 1,3-dihydropyrazole-2-carboxamide Chemical compound NC(=O)N1CC=CN1 PPVUWDCETZMPLT-UHFFFAOYSA-N 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 239000007858 starting material Substances 0.000 claims description 9
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 239000000969 carrier Substances 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
- ABULPTYCAANTCG-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(2,2-difluoro-1,3-benzodioxol-5-yl)-4-(4-fluorophenyl)-1,3-dihydropyrazole-2-carboxamide Chemical group C1=CC(F)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)NN(C(=O)NC=2C=C3OC(F)(F)OC3=CC=2)C1 ABULPTYCAANTCG-UHFFFAOYSA-N 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- UJMGZPCKYHBCKU-UHFFFAOYSA-N 2,2-dimethyl-2,3-dihydrobenzofuran Chemical compound C1=CC=C2OC(C)(C)CC2=C1 UJMGZPCKYHBCKU-UHFFFAOYSA-N 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 12
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims 3
- XBOBOUWNLXXMCE-UHFFFAOYSA-N N-methyl-4-phenyl-1,3-dihydropyrazole-2-carboxamide Chemical compound CNC(=O)N1NC=C(C1)C1=CC=CC=C1 XBOBOUWNLXXMCE-UHFFFAOYSA-N 0.000 claims 2
- ZTHCKGYGQCVNHZ-UHFFFAOYSA-N 4-phenyl-1,3-dihydropyrazole-2-carboxamide Chemical compound C1(=CC=CC=C1)C1=CNN(C1)C(=O)N ZTHCKGYGQCVNHZ-UHFFFAOYSA-N 0.000 claims 1
- NSIQNOIJNSJELJ-UHFFFAOYSA-N ClC1=CC=C(C=C1)C1=C(NN(C1)C=1C=CC2=C(CC(O2)(C)C)C1)C1=CC=CC=C1 Chemical group ClC1=CC=C(C=C1)C1=C(NN(C1)C=1C=CC2=C(CC(O2)(C)C)C1)C1=CC=CC=C1 NSIQNOIJNSJELJ-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 43
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 14
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 239000012141 concentrate Substances 0.000 description 10
- 235000008504 concentrate Nutrition 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 241000238631 Hexapoda Species 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000284 extract Substances 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 241000607479 Yersinia pestis Species 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- OHZVRWURXQTADI-UHFFFAOYSA-N N-(4-chlorophenyl)-1,3-dihydropyrazole-2-carboxamide Chemical compound N1(NC=CC1)C(=O)NC1=CC=C(C=C1)Cl OHZVRWURXQTADI-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229960000892 attapulgite Drugs 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- UQSZESXBGQDYKP-UHFFFAOYSA-N n-[4-(4-chlorophenoxy)phenyl]-5-(4-chlorophenyl)-4-phenyl-1,3-dihydropyrazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1OC(C=C1)=CC=C1NC(=O)N1NC(C=2C=CC(Cl)=CC=2)=C(C=2C=CC=CC=2)C1 UQSZESXBGQDYKP-UHFFFAOYSA-N 0.000 description 3
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
- 229910052625 palygorskite Inorganic materials 0.000 description 3
- 229910003446 platinum oxide Inorganic materials 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 229920005552 sodium lignosulfonate Polymers 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- LWDIQKVNWBXIMP-UHFFFAOYSA-N 2,2-dimethyl-3h-1-benzofuran-5-amine Chemical compound NC1=CC=C2OC(C)(C)CC2=C1 LWDIQKVNWBXIMP-UHFFFAOYSA-N 0.000 description 2
- IRMJENJPAMHVRK-UHFFFAOYSA-N 2,2-dimethyl-5-nitro-3h-1-benzofuran Chemical compound [O-][N+](=O)C1=CC=C2OC(C)(C)CC2=C1 IRMJENJPAMHVRK-UHFFFAOYSA-N 0.000 description 2
- YTISFYMPVILQRL-UHFFFAOYSA-N 4-(4-chlorophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(Cl)C=C1 YTISFYMPVILQRL-UHFFFAOYSA-N 0.000 description 2
- FBWKCZBSQZCRPW-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-phenyl-2,3-dihydro-1h-pyrazole Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C=CC=CC=2)CNN1 FBWKCZBSQZCRPW-UHFFFAOYSA-N 0.000 description 2
- IXSLSAQRJFXITM-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(2,2-dimethyl-3h-1-benzofuran-5-yl)-4-(4-fluorophenyl)-1,3-dihydropyrazole-2-carboxamide Chemical compound C=1C=C2OC(C)(C)CC2=CC=1NC(=O)N(N1)CC(C=2C=CC(F)=CC=2)=C1C1=CC=C(Cl)C=C1 IXSLSAQRJFXITM-UHFFFAOYSA-N 0.000 description 2
- MCNOQOMMAJGQGB-UHFFFAOYSA-N 5-[4-(difluoromethoxy)phenyl]-n-(2,2-dimethyl-3h-1-benzofuran-5-yl)-4-phenyl-1,3-dihydropyrazole-2-carboxamide Chemical compound C=1C=C2OC(C)(C)CC2=CC=1NC(=O)N(N1)CC(C=2C=CC=CC=2)=C1C1=CC=C(OC(F)F)C=C1 MCNOQOMMAJGQGB-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- 241000462639 Epilachna varivestis Species 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241001521235 Spodoptera eridania Species 0.000 description 2
- 241000256247 Spodoptera exigua Species 0.000 description 2
- 241000255993 Trichoplusia ni Species 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 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
- 235000014666 liquid concentrate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- ZWGWZRJPEBGVTK-UHFFFAOYSA-N n-(2,2-difluoro-1,3-benzodioxol-5-yl)-5-[4-(difluoromethoxy)phenyl]-n-methyl-4-phenyl-1,3-dihydropyrazole-2-carboxamide Chemical compound C=1C=C2OC(F)(F)OC2=CC=1N(C)C(=O)N(N1)CC(C=2C=CC=CC=2)=C1C1=CC=C(OC(F)F)C=C1 ZWGWZRJPEBGVTK-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 2
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- MJUVRTYWUMPBTR-MRXNPFEDSA-N 1-(2,2-difluoro-1,3-benzodioxol-5-yl)-n-[1-[(2r)-2,3-dihydroxypropyl]-6-fluoro-2-(1-hydroxy-2-methylpropan-2-yl)indol-5-yl]cyclopropane-1-carboxamide Chemical compound FC=1C=C2N(C[C@@H](O)CO)C(C(C)(CO)C)=CC2=CC=1NC(=O)C1(C=2C=C3OC(F)(F)OC3=CC=2)CC1 MJUVRTYWUMPBTR-MRXNPFEDSA-N 0.000 description 1
- ONGIGKVILBTLIY-UHFFFAOYSA-N 1-(2-bromo-1,1,2,2-tetrafluoroethoxy)-2-chloro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(OC(F)(F)C(F)(F)Br)C(Cl)=C1 ONGIGKVILBTLIY-UHFFFAOYSA-N 0.000 description 1
- GDEZSMXXDMVYHT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-4-nitrobenzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1 GDEZSMXXDMVYHT-UHFFFAOYSA-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
- CVYQRDKVWVBOFP-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxol-5-amine Chemical compound NC1=CC=C2OC(F)(F)OC2=C1 CVYQRDKVWVBOFP-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
- OUSKYXRCUNHVDY-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-2,3-dihydro-1h-pyrazole Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)NNC1 OUSKYXRCUNHVDY-UHFFFAOYSA-N 0.000 description 1
- NFRWJGUHQIZYOK-UHFFFAOYSA-N 4,5-diphenyl-n-(2,2,6-trimethyl-1,3-benzodioxol-5-yl)-1,3-dihydropyrazole-2-carboxamide Chemical compound CC1=CC=2OC(C)(C)OC=2C=C1NC(=O)N(N1)CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 NFRWJGUHQIZYOK-UHFFFAOYSA-N 0.000 description 1
- MHEWIIARNORUOK-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-5-(4-chlorophenyl)-n-(2,2-difluoro-1,3-benzodioxol-5-yl)-1,3-dihydropyrazole-2-carboxamide Chemical compound C1=C2OC(F)(F)OC2=CC=C1NC(=O)N(N1)CC(C=2C=C3OCOC3=CC=2)=C1C1=CC=C(Cl)C=C1 MHEWIIARNORUOK-UHFFFAOYSA-N 0.000 description 1
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- 239000012085 test solution Substances 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [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
- 238000009736 wetting Methods 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66467484A | 1984-10-25 | 1984-10-25 | |
| US70962685A | 1985-03-08 | 1985-03-08 | |
| US77972185A | 1985-09-24 | 1985-09-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT39073A HUT39073A (en) | 1986-08-28 |
| HU199808B true HU199808B (en) | 1990-03-28 |
Family
ID=27418114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU854103A HU199808B (en) | 1984-10-25 | 1985-10-24 | Process for producing pyrazoline derivatives and insecticides comprising pyrazoline derivatives as active ingredient |
Country Status (30)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3545786A1 (de) * | 1985-12-21 | 1987-06-25 | Schering Ag | Pyrazolinderivate, ihre herstellung und ihre verwendung als mittel mit insektizider wirkung |
| ZW9688A1 (en) * | 1987-07-17 | 1989-04-12 | Du Pont | Insecticidal pyrazolines |
| EP0367796A1 (en) * | 1987-07-17 | 1990-05-16 | E.I. Du Pont De Nemours And Company | Insecticidal pyrazolines |
| EP0437455A1 (en) * | 1988-09-22 | 1991-07-24 | E.I. Du Pont De Nemours And Company | Substituted indazole arthropodicides |
| JPH05112556A (ja) * | 1991-10-18 | 1993-05-07 | Nippon Bayeragrochem Kk | 殺虫性ピラゾリン類 |
| US5684041A (en) * | 1996-02-01 | 1997-11-04 | The Procter & Gamble Company | Dihydrobenzofuran and related compounds useful as anti-inflammatory agents |
| CN116265457B (zh) * | 2021-12-17 | 2024-09-03 | 湖南化工研究院有限公司 | N-氧杂稠环酰胺类化合物及其制备方法与应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE795264A (fr) * | 1972-02-09 | 1973-08-09 | Philips Nv | Nouveaux composes de pyrazoline a activite insecticide |
| NL158178B (nl) * | 1974-07-12 | 1978-10-16 | Philips Nv | Werkwijze ter bereiding van insekticide preparaten die een pyrazolinederivaat bevatten, aldus verkregen gevormde preparaten, en werkwijze ter bereiding van pyrazolinederivaten met insekticide werking. |
| US4174393A (en) * | 1975-07-09 | 1979-11-13 | Duphar International Research B.V. | 1,3,4-Substituted pyrazoline derivatives |
| NL183400C (nl) * | 1976-01-09 | 1988-10-17 | Duphar Int Res | Werkwijze ter bereiding van een insecticide preparaat dat een pyrazoline-verbinding bevat en werkwijze ter bereiding van een pyrazoline-verbinding met insecticide werking. |
| ATE4593T1 (de) * | 1979-07-03 | 1983-09-15 | Duphar International Research B.V | Pyrazolin-derivate, verfahren zur herstellung dieser verbindungen sowie insektizide zusammensetzung auf der basis dieser verbindungen. |
| 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 |
| EP0113213B1 (en) * | 1982-12-30 | 1988-04-06 | Schering Agrochemicals Limited | 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 CA493018A patent/CA1265145C/en not_active Expired
- 1985-10-21 IL IL76771A patent/IL76771A0/xx not_active IP Right Cessation
- 1985-10-23 LU LU86134A patent/LU86134A1/fr unknown
- 1985-10-23 AT AT0306085A patent/ATA306085A/de not_active Application Discontinuation
- 1985-10-23 AP APAP/P/1985/000014A patent/AP36A/en active
- 1985-10-23 GB GB08526175A patent/GB2166137B/en not_active Expired
- 1985-10-24 CN CN85107882.6A patent/CN1004272B/zh not_active Expired
- 1985-10-24 DK DK487885A patent/DK487885A/da not_active Application Discontinuation
- 1985-10-24 KR KR1019850007838A patent/KR880001568B1/ko not_active Expired
- 1985-10-24 BR BR8505326A patent/BR8505326A/pt unknown
- 1985-10-24 NZ NZ213953A patent/NZ213953A/xx unknown
- 1985-10-24 DE DE19853537884 patent/DE3537884A1/de not_active Ceased
- 1985-10-24 HU HU854103A patent/HU199808B/hu unknown
- 1985-10-24 ES ES548170A patent/ES8701757A1/es not_active Expired
- 1985-10-24 CS CS857615A patent/CS252497B2/cs unknown
- 1985-10-24 IT IT22601/85A patent/IT1203596B/it active
- 1985-10-24 CH CH4582/85A patent/CH666029A5/de not_active IP Right Cessation
- 1985-10-24 NL NL8502913A patent/NL8502913A/nl not_active Application Discontinuation
- 1985-10-24 SE SE8505026A patent/SE8505026L/xx not_active Application Discontinuation
- 1985-10-24 YU YU1686/85A patent/YU45287B/xx unknown
- 1985-10-25 FR FR8515890A patent/FR2572400A1/fr not_active Withdrawn
- 1985-10-25 OA OA58712A patent/OA08127A/xx unknown
- 1985-10-25 PL PL1985255938A patent/PL150265B1/pl unknown
- 1985-10-25 GR GR852585A patent/GR852585B/el unknown
- 1985-10-25 RO RO120544A patent/RO92966B/ro unknown
- 1985-10-25 BE BE0/215778A patent/BE903521A/fr not_active IP Right Cessation
- 1985-10-27 EG EG680/85A patent/EG17848A/xx active
-
1987
- 1987-09-29 MY MYPI87002197A patent/MY102602A/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |