CA1265145A - Pyrazoline insecticides - Google Patents
Pyrazoline insecticidesInfo
- Publication number
- CA1265145A CA1265145A CA000493018A CA493018A CA1265145A CA 1265145 A CA1265145 A CA 1265145A CA 000493018 A CA000493018 A CA 000493018A CA 493018 A CA493018 A CA 493018A CA 1265145 A CA1265145 A CA 1265145A
- Authority
- CA
- Canada
- Prior art keywords
- hydrogen
- halogen
- lower alkyl
- formula
- carboxamide
- 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 - Lifetime
Links
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 239000002917 insecticide Substances 0.000 title abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 80
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 66
- 239000001257 hydrogen Substances 0.000 claims abstract description 66
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 60
- 150000002367 halogens Chemical class 0.000 claims abstract description 60
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 46
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 37
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 36
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 34
- 241000238631 Hexapoda Species 0.000 claims abstract description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 239000001301 oxygen Substances 0.000 claims abstract description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000005133 alkynyloxy group Chemical group 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 239000011593 sulfur Substances 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 75
- 150000001875 compounds Chemical class 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 36
- -1 2,3-dihydro-2,2-dimethylbenzo-furan-5-yl Chemical group 0.000 claims description 28
- 230000000749 insecticidal effect Effects 0.000 claims description 17
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 4
- ARKLDSUYDZUISS-UHFFFAOYSA-N 5-[4-(difluoromethoxy)phenyl]-4-(4-fluorophenyl)-n-(2,2,3,3-tetrafluoro-1-benzofuran-5-yl)-1,3-dihydropyrazole-2-carboxamide Chemical compound C1=CC(OC(F)F)=CC=C1C1=C(C=2C=CC(F)=CC=2)CN(C(=O)NC=2C=C3C(F)(F)C(F)(F)OC3=CC=2)N1 ARKLDSUYDZUISS-UHFFFAOYSA-N 0.000 claims description 2
- STEJLBYIXIBCRM-UHFFFAOYSA-N 5-[4-(difluoromethoxy)phenyl]-4-phenyl-n-(2,2,3,3-tetrafluoro-1-benzofuran-5-yl)-1,3-dihydropyrazole-2-carboxamide Chemical compound C1=CC(OC(F)F)=CC=C1C1=C(C=2C=CC=CC=2)CN(C(=O)NC=2C=C3C(F)(F)C(F)(F)OC3=CC=2)N1 STEJLBYIXIBCRM-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims 1
- YFFDTVJESTUUIP-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-n-(2,2-dimethyl-1,3-benzodioxol-5-yl)-1,3-dihydropyrazole-2-carboxamide Chemical compound C1=C2OC(C)(C)OC2=CC=C1NC(=O)N(N1)CC(C=2C=CC(Cl)=CC=2)=C1C1=CC=C(Cl)C=C1 YFFDTVJESTUUIP-UHFFFAOYSA-N 0.000 claims 1
- HEHNQXBTAWAQEE-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-[4-(difluoromethoxy)phenyl]-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)N(N1)CC(C=2C=CC(Cl)=CC=2)=C1C1=CC=C(OC(F)F)C=C1 HEHNQXBTAWAQEE-UHFFFAOYSA-N 0.000 claims 1
- 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
- YNJVXBKIPWTBEV-UHFFFAOYSA-N 5-[4-(difluoromethoxy)phenyl]-4-(4-fluorophenyl)-n-(2,2,3,3-tetrafluoro-1-benzofuran-6-yl)-1,3-dihydropyrazole-2-carboxamide Chemical compound C1=CC(OC(F)F)=CC=C1C1=C(C=2C=CC(F)=CC=2)CN(C(=O)NC=2C=C3C(C(C(F)(F)O3)(F)F)=CC=2)N1 YNJVXBKIPWTBEV-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 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 1
- KQJUTCPRNOFWJL-UHFFFAOYSA-N n-[4-[4-(difluoromethoxy)phenoxy]phenyl]-5-[4-(difluoromethoxy)phenyl]-4-(4-fluorophenyl)-1,3-dihydropyrazole-2-carboxamide Chemical compound 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
- 150000003219 pyrazolines Chemical class 0.000 abstract description 24
- 230000001276 controlling effect Effects 0.000 abstract 1
- 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 28
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 24
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 22
- 239000000243 solution Substances 0.000 description 19
- 150000002500 ions Chemical class 0.000 description 13
- 101150041968 CDC13 gene Proteins 0.000 description 12
- 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
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 9
- 235000008504 concentrate Nutrition 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 239000000969 carrier Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- 150000003857 carboxamides Chemical class 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 239000002245 particle 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
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 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
- 241000255993 Trichoplusia ni Species 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229960000892 attapulgite Drugs 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
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000000463 material Substances 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
- 239000007921 spray Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 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
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000462639 Epilachna varivestis Species 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 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
- 241000607479 Yersinia pestis Species 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000001207 fluorophenyl group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 235000011167 hydrochloric acid Nutrition 0.000 description 2
- 229960000443 hydrochloric acid Drugs 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
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 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
- 229910003446 platinum oxide Inorganic materials 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
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-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
- 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
- KCIGEQYJXFMPQV-UHFFFAOYSA-N 1-(4-fluorophenyl)-3H-pyrazole-2-carboxamide Chemical compound FC1=CC=C(C=C1)N1N(CC=C1)C(=O)N KCIGEQYJXFMPQV-UHFFFAOYSA-N 0.000 description 1
- YWBWHAJXLMXHQZ-UHFFFAOYSA-N 1-(4-methylphenyl)-3H-pyrazole-2-carboxamide Chemical compound CC1=CC=C(C=C1)N1N(CC=C1)C(=O)N YWBWHAJXLMXHQZ-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
- 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
- FZKOBOYWZLSUOR-UHFFFAOYSA-N 3,5-bis(4-chlorophenyl)-n-[4-(3-fluorophenoxy)phenyl]-1,3-dihydropyrazole-2-carboxamide Chemical compound FC1=CC=CC(OC=2C=CC(NC(=O)N3C(C=C(N3)C=3C=CC(Cl)=CC=3)C=3C=CC(Cl)=CC=3)=CC=2)=C1 FZKOBOYWZLSUOR-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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- SZLWIDNRFWBNAP-UHFFFAOYSA-N n-[4-(3-chlorophenoxy)phenyl]-4,5-bis(4-chlorophenyl)-1,3-dihydropyrazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)NN(C(=O)NC=2C=CC(OC=3C=C(Cl)C=CC=3)=CC=2)C1 SZLWIDNRFWBNAP-UHFFFAOYSA-N 0.000 description 1
- YJVPBVUUWAAPKC-UHFFFAOYSA-N n-[4-(4-chlorophenoxy)phenyl]-4,5-bis(4-chlorophenyl)-1,3-dihydropyrazole-2-carbothioamide Chemical compound C1=CC(Cl)=CC=C1OC(C=C1)=CC=C1NC(=S)N1NC(C=2C=CC(Cl)=CC=2)=C(C=2C=CC(Cl)=CC=2)C1 YJVPBVUUWAAPKC-UHFFFAOYSA-N 0.000 description 1
- AUCLZTFCLRTNAK-UHFFFAOYSA-N n-[4-(4-chlorophenoxy)phenyl]-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=CC(OC=3C=CC(Cl)=CC=3)=CC=2)C1 AUCLZTFCLRTNAK-UHFFFAOYSA-N 0.000 description 1
- RDAFJUYDRXBKSC-UHFFFAOYSA-N n-[4-(4-chlorophenoxy)phenyl]-4-(2,2-difluoro-1,3-benzodioxol-5-yl)-5-phenyl-1,3-dihydropyrazole-2-carboxamide Chemical compound C1=C2OC(F)(F)OC2=CC=C1C(C1)=C(C=2C=CC=CC=2)NN1C(=O)NC(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 RDAFJUYDRXBKSC-UHFFFAOYSA-N 0.000 description 1
- GAHCUIPABMKBBN-UHFFFAOYSA-N n-[4-(4-chlorophenoxy)phenyl]-5-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-phenyl-1,3-dihydropyrazole-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1OC(C=C1)=CC=C1NC(=O)N1NC(C=2C=C3OCCOC3=CC=2)=C(C=2C=CC=CC=2)C1 GAHCUIPABMKBBN-UHFFFAOYSA-N 0.000 description 1
- AIFUJJZTHJIAFK-UHFFFAOYSA-N n-[4-(4-cyanophenoxy)phenyl]-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=CC(OC=3C=CC(=CC=3)C#N)=CC=2)C1 AIFUJJZTHJIAFK-UHFFFAOYSA-N 0.000 description 1
- DWGZHNKMRRWYIC-UHFFFAOYSA-N n-[4-(4-methylsulfonylphenoxy)phenyl]-4,5-diphenyl-1,3-dihydropyrazole-2-carboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC(C=C1)=CC=C1NC(=O)N1NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C1 DWGZHNKMRRWYIC-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 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
- 238000002360 preparation method Methods 0.000 description 1
- TURAMGVWNUTQKH-UHFFFAOYSA-N propa-1,2-dien-1-one Chemical group C=C=C=O TURAMGVWNUTQKH-UHFFFAOYSA-N 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000001508 sulfur Nutrition 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 239000008096 xylene 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
- 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA493018A CA1265145C (en) | 1984-10-25 | 1985-10-16 | PYRAZOLINE INSECTICIDES |
Applications Claiming Priority (7)
| 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 | ||
| CA493018A CA1265145C (en) | 1984-10-25 | 1985-10-16 | PYRAZOLINE INSECTICIDES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA1265145A true CA1265145A (en) | 1990-01-30 |
| CA1265145C CA1265145C (en) | 1990-01-30 |
Family
ID=27418114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA493018A Expired CA1265145C (en) | 1984-10-25 | 1985-10-16 | 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 |
| 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 |
| 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. |
| EP0021506B1 (en) * | 1979-07-03 | 1983-09-07 | Duphar International Research B.V | New pyrazoline derivatives, method of preparing the new compounds, as well as insecticidal composition on the basis of these new compounds |
| US4407813A (en) * | 1981-02-17 | 1983-10-04 | Nissan Chemical Industries Ltd. | Insecticidal pyrazoline derivatives and composition |
| 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 CA CA493018A patent/CA1265145C/en not_active Expired
- 1985-10-16 IN IN864/DEL/85A patent/IN166473B/en unknown
- 1985-10-21 IL IL76771A patent/IL76771A0/xx not_active IP Right Cessation
- 1985-10-23 AT AT0306085A patent/ATA306085A/de not_active Application Discontinuation
- 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 LU LU86134A patent/LU86134A1/fr unknown
- 1985-10-24 NZ NZ213953A patent/NZ213953A/xx unknown
- 1985-10-24 KR KR1019850007838A patent/KR880001568B1/ko not_active Expired
- 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 CN CN85107882.6A patent/CN1004272B/zh not_active Expired
- 1985-10-24 ES ES548170A patent/ES8701757A1/es not_active Expired
- 1985-10-24 HU HU854103A patent/HU199808B/hu unknown
- 1985-10-24 SE SE8505026A patent/SE8505026L/xx not_active Application Discontinuation
- 1985-10-24 BR BR8505326A patent/BR8505326A/pt unknown
- 1985-10-24 CS CS857615A patent/CS252497B2/cs unknown
- 1985-10-24 DK DK487885A patent/DK487885A/da not_active Application Discontinuation
- 1985-10-24 DE DE19853537884 patent/DE3537884A1/de not_active Ceased
- 1985-10-24 IT IT22601/85A patent/IT1203596B/it active
- 1985-10-24 YU YU1686/85A patent/YU45287B/xx unknown
- 1985-10-25 BE BE0/215778A patent/BE903521A/fr not_active IP Right Cessation
- 1985-10-25 GR GR852585A patent/GR852585B/el unknown
- 1985-10-25 FR FR8515890A patent/FR2572400A1/fr not_active Withdrawn
- 1985-10-25 RO RO120544A patent/RO92966B/ro unknown
- 1985-10-25 OA OA58712A patent/OA08127A/xx unknown
- 1985-10-25 PL PL1985255938A patent/PL150265B1/pl unknown
- 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 |
|---|---|---|---|
| MKLA | Lapsed | ||
| MKLA | Lapsed |
Effective date: 19930731 |