AP36A - Pyrazoline insecticides - Google Patents
Pyrazoline insecticides Download PDFInfo
- Publication number
- AP36A AP36A APAP/P/1985/000014A AP8500014A AP36A AP 36 A AP36 A AP 36A AP 8500014 A AP8500014 A AP 8500014A AP 36 A AP36 A AP 36A
- Authority
- AP
- ARIPO
- Prior art keywords
- hydrogen
- halogen
- formula
- lower alkyl
- compound
- Prior art date
Links
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 239000002917 insecticide Substances 0.000 title claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 76
- 229910052739 hydrogen Inorganic materials 0.000 claims description 67
- 239000001257 hydrogen Substances 0.000 claims description 67
- 229910052736 halogen Inorganic materials 0.000 claims description 60
- 150000002367 halogens Chemical class 0.000 claims description 59
- 150000001875 compounds Chemical class 0.000 claims description 48
- 150000002431 hydrogen Chemical class 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 38
- 125000003545 alkoxy group Chemical group 0.000 claims description 37
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 35
- 125000001188 haloalkyl group Chemical group 0.000 claims description 32
- 150000003219 pyrazolines Chemical class 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- -1 hydro halogen Chemical class 0.000 claims description 17
- 241000238631 Hexapoda Species 0.000 claims description 16
- 230000000749 insecticidal effect Effects 0.000 claims description 16
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 10
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000005133 alkynyloxy group Chemical group 0.000 claims 5
- 241000282320 Panthera leo Species 0.000 claims 2
- USBQOONERNJYKY-UHFFFAOYSA-N 4,5-bis(4-fluorophenyl)-n-(2,2,3,3-tetrafluoro-1-benzofuran-5-yl)-1,3-dihydropyrazole-2-carboxamide Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CC(F)=CC=2)NN(C(=O)NC=2C=C3C(F)(F)C(F)(F)OC3=CC=2)C1 USBQOONERNJYKY-UHFFFAOYSA-N 0.000 claims 1
- IFMDMFBBMTXOED-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-(2,2-dimethyl-3h-1-benzofuran-5-yl)-5-phenyl-1,3-dihydropyrazole-2-carboxamide Chemical compound C=1C=C2OC(C)(C)CC2=CC=1NC(=O)N(N1)CC(C=2C=CC(Cl)=CC=2)=C1C1=CC=CC=C1 IFMDMFBBMTXOED-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 102100040141 Aminopeptidase O Human genes 0.000 claims 1
- 108050008333 Aminopeptidase O Proteins 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 229940099990 ogen Drugs 0.000 claims 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 23
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 9
- 235000008504 concentrate Nutrition 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- 239000000969 carrier Substances 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 150000003857 carboxamides Chemical class 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 5
- 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002689 soil 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 241000462639 Epilachna varivestis Species 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 241001521235 Spodoptera eridania Species 0.000 description 3
- 241000255993 Trichoplusia ni Species 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229960000892 attapulgite Drugs 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000000463 material Substances 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
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 229940086542 triethylamine Drugs 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- 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 2
- 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 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 description 2
- PUDNABSYXBYBRZ-UHFFFAOYSA-N 5-(4-chlorophenyl)-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(Cl)C=C1 PUDNABSYXBYBRZ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 241000256247 Spodoptera exigua Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000005843 halogen group Chemical group 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
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 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
- 238000000746 purification Methods 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 239000012085 test solution Substances 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
- 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
- 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
- UWMILPOJVHLRBZ-UHFFFAOYSA-N 2,2,3,3-tetrafluoro-5-nitro-1-benzofuran Chemical compound [O-][N+](=O)C1=CC=C2OC(F)(F)C(F)(F)C2=C1 UWMILPOJVHLRBZ-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
- UJMGZPCKYHBCKU-UHFFFAOYSA-N 2,2-dimethyl-2,3-dihydrobenzofuran Chemical compound C1=CC=C2OC(C)(C)CC2=C1 UJMGZPCKYHBCKU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- HJUFKPWPTLOJKV-UHFFFAOYSA-N 3,5-bis(4-chlorophenyl)-n-(2,2-dimethyl-3h-1-benzofuran-5-yl)-1,3-dihydropyrazole-2-carboxamide Chemical compound C=1C=C2OC(C)(C)CC2=CC=1NC(=O)N1NC(C=2C=CC(Cl)=CC=2)=CC1C1=CC=C(Cl)C=C1 HJUFKPWPTLOJKV-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
- 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
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- HVDQTFIHZALRTL-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-n-(2,2-dimethyl-3h-1-benzofuran-5-yl)-n-methyl-1,3-dihydropyrazole-2-carboxamide Chemical compound C=1C=C2OC(C)(C)CC2=CC=1N(C)C(=O)N(N1)CC(C=2C=CC(Cl)=CC=2)=C1C1=CC=C(Cl)C=C1 HVDQTFIHZALRTL-UHFFFAOYSA-N 0.000 description 1
- SMDRCXHZNVYZCL-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-n-(2,3-dihydro-1-benzofuran-5-yl)-1,3-dihydropyrazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)NN(C(=O)NC=2C=C3CCOC3=CC=2)C1 SMDRCXHZNVYZCL-UHFFFAOYSA-N 0.000 description 1
- JBSJGLRUKBCQFG-UHFFFAOYSA-N 4-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-phenyl-n-(2,2,3,3-tetrafluoro-1-benzofuran-5-yl)-1,3-dihydropyrazole-2-carboxamide Chemical compound C1=C2C(F)(F)C(F)(F)OC2=CC=C1NC(=O)N(N1)CC(C=2C=C3OCCOC3=CC=2)=C1C1=CC=CC=C1 JBSJGLRUKBCQFG-UHFFFAOYSA-N 0.000 description 1
- JXFTZUAMGFFRTQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-[4-(difluoromethoxy)phenyl]-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-1,3-dihydropyrazole-2-carboxamide Chemical compound C1=CC(OC(F)F)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)CN(C(=O)NC=2C=C3OCCOC3=CC=2)N1 JXFTZUAMGFFRTQ-UHFFFAOYSA-N 0.000 description 1
- CYMBYMDEENJFBK-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-(2,2-dimethyl-3h-1-benzofuran-5-yl)-5-(4-methoxyphenyl)-1,3-dihydropyrazole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)CN(C(=O)NC=2C=C3CC(C)(C)OC3=CC=2)N1 CYMBYMDEENJFBK-UHFFFAOYSA-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
- LNZDCAYAKXNHJE-UHFFFAOYSA-N 5,5,6,6-tetrafluoro-2-nitrocyclohexa-1,3-diene Chemical compound [O-][N+](=O)C1=CC(F)(F)C(F)(F)C=C1 LNZDCAYAKXNHJE-UHFFFAOYSA-N 0.000 description 1
- RDGRNOJKSCCLHW-UHFFFAOYSA-N 5-(1,3-benzodioxol-5-yl)-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(NC=1C=2C=C3OCOC3=CC=2)CC=1C1=CC=CC=C1 RDGRNOJKSCCLHW-UHFFFAOYSA-N 0.000 description 1
- PQAJTBKQXSBFJW-UHFFFAOYSA-N 5-(1,3-benzodioxol-5-yl)-n-(4-phenoxyphenyl)-4-phenyl-1,3-dihydropyrazole-2-carboxamide Chemical compound C1C(C=2C=CC=CC=2)=C(C=2C=C3OCOC3=CC=2)NN1C(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 PQAJTBKQXSBFJW-UHFFFAOYSA-N 0.000 description 1
- 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 1
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- 125000004432 carbon atom Chemical group C* 0.000 description 1
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- RCIYDBGRYPBHEN-UHFFFAOYSA-N n-(2,2-dimethyl-3h-1-benzofuran-5-yl)-4,5-diphenyl-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=CC=C1 RCIYDBGRYPBHEN-UHFFFAOYSA-N 0.000 description 1
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- 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 1
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- 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
- 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
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- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
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- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
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- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- 150000005846 sugar alcohols Polymers 0.000 description 1
- 235000001508 sulfur Nutrition 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 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
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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 |
|---|---|
| AP8500014A0 AP8500014A0 (en) | 1985-08-01 |
| AP36A true AP36A (en) | 1988-12-06 |
Family
ID=27418114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1985/000014A AP36A (en) | 1984-10-25 | 1985-10-23 | Pyrazoline insecticides |
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 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4174393A (en) * | 1975-07-09 | 1979-11-13 | Duphar International Research B.V. | 1,3,4-Substituted pyrazoline derivatives |
| CA1075242A (en) * | 1974-07-12 | 1980-04-08 | N.V. Philips Gloeilampenfabrieken | 1,3,4-substituted-.delta.2-pyrazoline compounds |
| CA1111048A (en) * | 1976-01-09 | 1981-10-20 | Jan J. Van Daalen | 1,3,4 substituted pyrazoline derivatives |
| US4407813A (en) * | 1981-02-17 | 1983-10-04 | Nissan Chemical Industries Ltd. | Insecticidal pyrazoline derivatives and composition |
Family Cites Families (4)
| 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 |
| 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 |
| 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
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1075242A (en) * | 1974-07-12 | 1980-04-08 | N.V. Philips Gloeilampenfabrieken | 1,3,4-substituted-.delta.2-pyrazoline compounds |
| US4174393A (en) * | 1975-07-09 | 1979-11-13 | Duphar International Research B.V. | 1,3,4-Substituted pyrazoline derivatives |
| CA1111048A (en) * | 1976-01-09 | 1981-10-20 | Jan J. Van Daalen | 1,3,4 substituted pyrazoline derivatives |
| US4407813A (en) * | 1981-02-17 | 1983-10-04 | Nissan Chemical Industries Ltd. | Insecticidal pyrazoline derivatives and composition |
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