JPS61106558A - ピラゾリン殺虫剤 - Google Patents
ピラゾリン殺虫剤Info
- Publication number
- JPS61106558A JPS61106558A JP23551385A JP23551385A JPS61106558A JP S61106558 A JPS61106558 A JP S61106558A JP 23551385 A JP23551385 A JP 23551385A JP 23551385 A JP23551385 A JP 23551385A JP S61106558 A JPS61106558 A JP S61106558A
- Authority
- JP
- Japan
- Prior art keywords
- carboxamide
- pyrazoline
- formula
- dihydro
- halogen
- 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.)
- Granted
Links
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 title claims description 12
- 239000002917 insecticide Substances 0.000 title description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- -1 2,3-dihydro-2,2-dimethylbenzofuran-5-yl Chemical group 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 43
- 229910052736 halogen Inorganic materials 0.000 claims description 41
- 150000002367 halogens Chemical class 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 31
- 150000002431 hydrogen Chemical class 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 24
- 125000001188 haloalkyl group Chemical group 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 23
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 17
- PPVUWDCETZMPLT-UHFFFAOYSA-N 1,3-dihydropyrazole-2-carboxamide Chemical compound NC(=O)N1CC=CN1 PPVUWDCETZMPLT-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 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
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- QNYTVFQMOJTRAD-UHFFFAOYSA-N 5-phenyl-1,3-dihydropyrazole-2-carboxamide Chemical compound C1(=CC=CC=C1)C=1NN(CC=1)C(=O)N QNYTVFQMOJTRAD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims description 2
- QSHVRMBMYMRGKV-UHFFFAOYSA-N n-(2,2-difluoro-1,3-benzodioxol-5-yl)-4,5-bis(4-fluorophenyl)-1,3-dihydropyrazole-2-carboxamide Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CC(F)=CC=2)NN(C(=O)NC=2C=C3OC(F)(F)OC3=CC=2)C1 QSHVRMBMYMRGKV-UHFFFAOYSA-N 0.000 claims description 2
- 230000000361 pesticidal effect Effects 0.000 claims 2
- 230000002152 alkylating effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- KQJUTCPRNOFWJL-UHFFFAOYSA-N n-[4-[4-(difluoromethoxy)phenoxy]phenyl]-5-[4-(difluoromethoxy)phenyl]-4-(4-fluorophenyl)-1,3-dihydropyrazole-2-carboxamide Chemical class C1=CC(OC(F)F)=CC=C1OC(C=C1)=CC=C1NC(=O)N1NC(C=2C=CC(OC(F)F)=CC=2)=C(C=2C=CC(F)=CC=2)C1 KQJUTCPRNOFWJL-UHFFFAOYSA-N 0.000 claims 1
- 230000001629 suppression Effects 0.000 claims 1
- 230000008018 melting Effects 0.000 description 119
- 238000002844 melting Methods 0.000 description 119
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- 150000003219 pyrazolines Chemical class 0.000 description 21
- 230000000749 insecticidal effect Effects 0.000 description 15
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- 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 12
- 241000238631 Hexapoda Species 0.000 description 11
- 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 8
- 235000008504 concentrate Nutrition 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- 239000000969 carrier Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000003857 carboxamides Chemical class 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000004927 clay Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 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 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 125000000068 chlorophenyl group Chemical group 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 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
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 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
- 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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical group [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229960000892 attapulgite Drugs 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
- 238000004440 column chromatography Methods 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000001207 fluorophenyl group Chemical group 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 3
- 229910052625 palygorskite Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 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 2
- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 2
- JQJRLXMKVFWXBP-UHFFFAOYSA-N 5-[4-(difluoromethoxy)phenyl]-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(OC(F)F)C=C1 JQJRLXMKVFWXBP-UHFFFAOYSA-N 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 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
- 241001477931 Mythimna unipuncta Species 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000003197 catalytic effect Effects 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
- 230000000694 effects Effects 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 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
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 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
- 229910052903 pyrophyllite Inorganic materials 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent 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
- 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
- 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
- HAWUINBKLOXNCI-UHFFFAOYSA-N 1-(2,2-dimethyl-3H-1-benzofuran-5-yl)-3H-pyrazole-2-carboxamide Chemical compound CC1(OC2=C(C1)C=C(C=C2)N1N(CC=C1)C(=O)N)C HAWUINBKLOXNCI-UHFFFAOYSA-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
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 1
- GFDJEJFDDZSGCB-UHFFFAOYSA-N 1-phenyl-3H-pyrazole-2-carboxamide Chemical compound C1(=CC=CC=C1)N1N(CC=C1)C(N)=O GFDJEJFDDZSGCB-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
- 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
- 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 1
- YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 1
- PTSLUOSUHFGQHV-UHFFFAOYSA-N 2-chloroheptane Chemical compound CCCCCC(C)Cl PTSLUOSUHFGQHV-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- NHWKQVDURCJFOP-UHFFFAOYSA-N 3,5-bis(4-chlorophenyl)-n-(2,3-dihydro-1,4-benzodioxin-6-yl)-1,3-dihydropyrazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1N(C(=O)NC=2C=C3OCCOC3=CC=2)NC(C=2C=CC(Cl)=CC=2)=C1 NHWKQVDURCJFOP-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
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Landscapes
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- Plural Heterocyclic Compounds (AREA)
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Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66467484A | 1984-10-25 | 1984-10-25 | |
| US709626 | 1985-03-08 | ||
| US779721 | 1985-09-24 | ||
| US664674 | 2003-09-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61106558A true JPS61106558A (ja) | 1986-05-24 |
| JPS6326109B2 JPS6326109B2 (enrdf_load_stackoverflow) | 1988-05-27 |
Family
ID=24666966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23551385A Granted JPS61106558A (ja) | 1984-10-25 | 1985-10-23 | ピラゾリン殺虫剤 |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS61106558A (enrdf_load_stackoverflow) |
| GT (1) | GT198500107A (enrdf_load_stackoverflow) |
| TR (1) | TR24530A (enrdf_load_stackoverflow) |
| ZA (1) | ZA858002B (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62228064A (ja) * | 1985-12-21 | 1987-10-06 | シエ−リング・アクチエンゲゼルシヤフト | ピラゾリン−誘導体、その製法及びこれを含有する殺虫及びダニ駆除剤 |
| JP2005325118A (ja) * | 2004-05-14 | 2005-11-24 | Lanxess Deutschland Gmbh | ジフルオロベンゾ−［１，３］−ジオキソール |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5287166A (en) * | 1976-01-09 | 1977-07-20 | Philips Nv | 1*3*44substituted pyrazoline derivatives and preparation thereof |
-
1985
- 1985-10-17 ZA ZA858002A patent/ZA858002B/xx unknown
- 1985-10-23 JP JP23551385A patent/JPS61106558A/ja active Granted
- 1985-10-24 GT GT198500107A patent/GT198500107A/es unknown
- 1985-10-25 TR TR4299685A patent/TR24530A/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5287166A (en) * | 1976-01-09 | 1977-07-20 | Philips Nv | 1*3*44substituted pyrazoline derivatives and preparation thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62228064A (ja) * | 1985-12-21 | 1987-10-06 | シエ−リング・アクチエンゲゼルシヤフト | ピラゾリン−誘導体、その製法及びこれを含有する殺虫及びダニ駆除剤 |
| JP2005325118A (ja) * | 2004-05-14 | 2005-11-24 | Lanxess Deutschland Gmbh | ジフルオロベンゾ−［１，３］−ジオキソール |
Also Published As
| Publication number | Publication date |
|---|---|
| TR24530A (tr) | 1991-11-20 |
| JPS6326109B2 (enrdf_load_stackoverflow) | 1988-05-27 |
| ZA858002B (en) | 1987-04-29 |
| GT198500107A (es) | 1987-04-17 |
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