SE444936B - Imidazolinderivat, forfarande for framstellning derav, pesticida beredningar innehallande imidazolinderivatet samt anvendning av derivatet som medel for bekempning av artropodaskadegorare - Google Patents
Imidazolinderivat, forfarande for framstellning derav, pesticida beredningar innehallande imidazolinderivatet samt anvendning av derivatet som medel for bekempning av artropodaskadegorareInfo
- Publication number
- SE444936B SE444936B SE7905374A SE7905374A SE444936B SE 444936 B SE444936 B SE 444936B SE 7905374 A SE7905374 A SE 7905374A SE 7905374 A SE7905374 A SE 7905374A SE 444936 B SE444936 B SE 444936B
- Authority
- SE
- Sweden
- Prior art keywords
- imidazoline
- compound
- carbamoyl
- formula
- carbon atoms
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 26
- 241000238421 Arthropoda Species 0.000 title claims description 5
- 238000000034 method Methods 0.000 title description 8
- 150000002462 imidazolines Chemical class 0.000 title description 3
- 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 51
- -1 (N-4-chlorophenyl) carbamoyl Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 7
- 241000607479 Yersinia pestis Species 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- 239000000575 pesticide Substances 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 4
- 239000004563 wettable powder Substances 0.000 claims description 4
- OBTMPVYDTRKARD-UHFFFAOYSA-N 2-[(2,3-dimethylphenoxy)methyl]-n-(4-methoxyphenyl)-4,5-dihydroimidazole-1-carboxamide Chemical group C1=CC(OC)=CC=C1NC(=O)N1C(COC=2C(=C(C)C=CC=2)C)=NCC1 OBTMPVYDTRKARD-UHFFFAOYSA-N 0.000 claims description 3
- 239000007900 aqueous suspension Substances 0.000 claims description 3
- 239000000428 dust Substances 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 239000000460 chlorine Substances 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- NZCCHKPAMIQOJJ-UHFFFAOYSA-N N-(4-bromophenyl)-2-[(2,3-dimethylanilino)methyl]-4,5-dihydroimidazole-1-carboxamide Chemical compound BrC1=CC=C(C=C1)NC(=O)N1C(=NCC1)CNC1=C(C(=CC=C1)C)C NZCCHKPAMIQOJJ-UHFFFAOYSA-N 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 235000013861 fat-free Nutrition 0.000 claims 1
- 239000000499 gel Substances 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000006072 paste Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000000375 suspending agent Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
- 239000002585 base Substances 0.000 description 8
- 241000238876 Acari Species 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WAAAGQHQBWTGTM-UHFFFAOYSA-N 2-[(2,3-dimethylphenoxy)methyl]-4,5-dihydro-1h-imidazole Chemical compound CC1=CC=CC(OCC=2NCCN=2)=C1C WAAAGQHQBWTGTM-UHFFFAOYSA-N 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000007598 dipping method Methods 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- GIBUUMBLBQUETG-UHFFFAOYSA-N n-(4-bromophenyl)-2-[(2,3-dimethylphenoxy)methyl]-4,5-dihydroimidazole-1-carboxamide Chemical compound CC1=CC=CC(OCC=2N(CCN=2)C(=O)NC=2C=CC(Br)=CC=2)=C1C GIBUUMBLBQUETG-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- NCWQZRJXZSACLY-UHFFFAOYSA-N 2-[(2,3-dimethylphenoxy)methyl]-n-(4-nitrophenyl)-4,5-dihydroimidazole-1-carboxamide Chemical compound CC1=CC=CC(OCC=2N(CCN=2)C(=O)NC=2C=CC(=CC=2)[N+]([O-])=O)=C1C NCWQZRJXZSACLY-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000238680 Rhipicephalus microplus Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- JGEBJBFRPSPWHR-UHFFFAOYSA-N n-(4-chlorophenyl)-2-[(2,3-dimethylanilino)methyl]-4,5-dihydroimidazole-1-carboxamide Chemical compound CC1=CC=CC(NCC=2N(CCN=2)C(=O)NC=2C=CC(Cl)=CC=2)=C1C JGEBJBFRPSPWHR-UHFFFAOYSA-N 0.000 description 2
- 239000003090 pesticide formulation Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- VYKNVAHOUNIVTQ-UHFFFAOYSA-N 1,2,2,3,3-pentamethylpiperidine Chemical compound CN1CCCC(C)(C)C1(C)C VYKNVAHOUNIVTQ-UHFFFAOYSA-N 0.000 description 1
- YAXWOADCWUUUNX-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine Chemical compound CC1CCCN(C)C1(C)C YAXWOADCWUUUNX-UHFFFAOYSA-N 0.000 description 1
- YIGYLPIXRNNTOA-UHFFFAOYSA-N 1-[(2,3-dimethylphenoxy)methyl]-4,5-dihydroimidazole Chemical compound CC1=C(OCN2C=NCC2)C=CC=C1C YIGYLPIXRNNTOA-UHFFFAOYSA-N 0.000 description 1
- CZQIJQFTRGDODI-UHFFFAOYSA-N 1-bromo-4-isocyanatobenzene Chemical compound BrC1=CC=C(N=C=O)C=C1 CZQIJQFTRGDODI-UHFFFAOYSA-N 0.000 description 1
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
- XMWOQBUECCSBEN-UHFFFAOYSA-N 2-(2,3-dimethylphenoxy)-4,5-dihydro-1h-imidazole Chemical compound CC1=CC=CC(OC=2NCCN=2)=C1C XMWOQBUECCSBEN-UHFFFAOYSA-N 0.000 description 1
- UNGNCSGRWHERGP-UHFFFAOYSA-N 2-[(2,3-dimethylphenoxy)methyl]-n-(4-fluorophenyl)-4,5-dihydroimidazole-1-carboxamide Chemical compound CC1=CC=CC(OCC=2N(CCN=2)C(=O)NC=2C=CC(F)=CC=2)=C1C UNGNCSGRWHERGP-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- HFGHRUCCKVYFKL-UHFFFAOYSA-N 4-ethoxy-2-piperazin-1-yl-7-pyridin-4-yl-5h-pyrimido[5,4-b]indole Chemical compound C1=C2NC=3C(OCC)=NC(N4CCNCC4)=NC=3C2=CC=C1C1=CC=NC=C1 HFGHRUCCKVYFKL-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241001480736 Amblyomma hebraeum Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- UKOOUFDVPQZLBF-UHFFFAOYSA-N N-(4-cyanophenyl)-2-[(2,3-dimethylanilino)methyl]-4,5-dihydroimidazole-1-carboxamide Chemical compound C(#N)C1=CC=C(C=C1)NC(=O)N1C(=NCC1)CNC1=C(C(=CC=C1)C)C UKOOUFDVPQZLBF-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241001649230 Psoroptes ovis Species 0.000 description 1
- 241001481704 Rhipicephalus appendiculatus Species 0.000 description 1
- 241000864246 Rhipicephalus decoloratus Species 0.000 description 1
- 241000864202 Rhipicephalus evertsi Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241001454294 Tetranychus Species 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 244000078703 ectoparasite Species 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- NNHREFKAXJZADC-UHFFFAOYSA-N ethyl 4-[[2-[(2,3-dimethylphenoxy)methyl]-4,5-dihydroimidazole-1-carbonyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)N1C(COC=2C(=C(C)C=CC=2)C)=NCC1 NNHREFKAXJZADC-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- WLUCWSITOBZYRR-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-ylmethyl)-2,3-dimethylaniline Chemical compound CC1=CC=CC(NCC=2NCCN=2)=C1C WLUCWSITOBZYRR-UHFFFAOYSA-N 0.000 description 1
- YENCJCFCSPYZRS-UHFFFAOYSA-N n-(4-bromophenyl)-2-[(2,3-dimethylphenoxy)methyl]-4,5-dihydroimidazole-1-carboxamide;hydrate Chemical compound O.CC1=CC=CC(OCC=2N(CCN=2)C(=O)NC=2C=CC(Br)=CC=2)=C1C YENCJCFCSPYZRS-UHFFFAOYSA-N 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000004540 pour-on Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/24—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- 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
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/22—Radicals substituted by oxygen atoms
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7827295 | 1978-06-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7905374L SE7905374L (sv) | 1979-12-20 |
| SE444936B true SE444936B (sv) | 1986-05-20 |
Family
ID=10498035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7905374A SE444936B (sv) | 1978-06-19 | 1979-06-19 | Imidazolinderivat, forfarande for framstellning derav, pesticida beredningar innehallande imidazolinderivatet samt anvendning av derivatet som medel for bekempning av artropodaskadegorare |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS554389A (de) |
| AR (1) | AR228841A1 (de) |
| AU (1) | AU525698B2 (de) |
| BE (1) | BE877094R (de) |
| BR (1) | BR7903857A (de) |
| CA (1) | CA1108621A (de) |
| CH (1) | CH643544A5 (de) |
| DE (1) | DE2924715A1 (de) |
| DK (1) | DK255879A (de) |
| ES (3) | ES481670A2 (de) |
| FR (1) | FR2429206A2 (de) |
| HU (1) | HU184221B (de) |
| IE (1) | IE48760B1 (de) |
| IT (1) | IT1162645B (de) |
| LU (1) | LU81394A1 (de) |
| MW (1) | MW1679A1 (de) |
| NL (1) | NL7904810A (de) |
| SE (1) | SE444936B (de) |
| ZA (1) | ZA787351B (de) |
| ZM (1) | ZM5379A1 (de) |
| ZW (1) | ZW12079A1 (de) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH529766A (de) * | 1967-02-23 | 1972-10-31 | Horst Prof Baganz | Verfahren zur Herstellung von Aryloxy-isoalkyl- 2-imidazolinen |
| GB1469772A (en) * | 1973-06-21 | 1977-04-06 | Boots Co Ltd | Fungicidal imidazole derivatives |
| GB1486192A (en) * | 1973-11-19 | 1977-09-21 | Boots Co Ltd | Imidazole derivatives |
| NL7712401A (nl) * | 1976-11-16 | 1978-05-18 | Ciba Geigy | Werkwijze voor het bereiden van preparaten voor het bestrijden van schadelijke organismen. |
| JPS5395968A (en) * | 1976-12-20 | 1978-08-22 | Wellcome Found | Imidazoline compounds |
| JPS5484575A (en) * | 1977-10-26 | 1979-07-05 | Wellcome Found | Imidazoline compound*its manufacture and insecticide composition |
-
1978
- 1978-12-28 ZA ZA787351A patent/ZA787351B/xx unknown
-
1979
- 1979-06-16 ZM ZM53/79A patent/ZM5379A1/xx unknown
- 1979-06-18 LU LU81394A patent/LU81394A1/fr unknown
- 1979-06-19 AU AU48201/79A patent/AU525698B2/en not_active Expired
- 1979-06-19 DK DK255879A patent/DK255879A/da not_active Application Discontinuation
- 1979-06-19 DE DE19792924715 patent/DE2924715A1/de not_active Ceased
- 1979-06-19 FR FR7915663A patent/FR2429206A2/fr active Granted
- 1979-06-19 ES ES481670A patent/ES481670A2/es not_active Expired
- 1979-06-19 AR AR276980A patent/AR228841A1/es active
- 1979-06-19 HU HU79WE601A patent/HU184221B/hu not_active IP Right Cessation
- 1979-06-19 CA CA330,075A patent/CA1108621A/en not_active Expired
- 1979-06-19 JP JP7746379A patent/JPS554389A/ja active Granted
- 1979-06-19 BR BR7903857A patent/BR7903857A/pt unknown
- 1979-06-19 MW MW16/79A patent/MW1679A1/xx unknown
- 1979-06-19 NL NL7904810A patent/NL7904810A/xx not_active Application Discontinuation
- 1979-06-19 SE SE7905374A patent/SE444936B/sv not_active IP Right Cessation
- 1979-06-19 IT IT49462/79A patent/IT1162645B/it active
- 1979-06-19 CH CH571779A patent/CH643544A5/de not_active IP Right Cessation
- 1979-06-19 BE BE0/195834A patent/BE877094R/xx not_active IP Right Cessation
- 1979-06-19 ZW ZW120/79A patent/ZW12079A1/xx unknown
- 1979-08-08 IE IE1153/79A patent/IE48760B1/en unknown
-
1980
- 1980-03-17 ES ES489642A patent/ES8400413A2/es not_active Expired
- 1980-03-17 ES ES489641A patent/ES489641A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| ES489642A0 (es) | 1983-10-16 |
| AR228841A1 (es) | 1983-04-29 |
| ZW12079A1 (en) | 1981-01-21 |
| IE791153L (en) | 1979-12-19 |
| IT1162645B (it) | 1987-04-01 |
| CH643544A5 (en) | 1984-06-15 |
| CA1108621A (en) | 1981-09-08 |
| DK255879A (da) | 1979-12-20 |
| ES481670A2 (es) | 1980-06-16 |
| FR2429206A2 (fr) | 1980-01-18 |
| DE2924715A1 (de) | 1980-01-03 |
| BE877094R (fr) | 1979-12-19 |
| JPS623836B2 (de) | 1987-01-27 |
| SE7905374L (sv) | 1979-12-20 |
| NL7904810A (nl) | 1979-12-21 |
| BR7903857A (pt) | 1980-03-04 |
| ES8104240A1 (es) | 1981-04-01 |
| LU81394A1 (fr) | 1980-01-22 |
| IT7949462A0 (it) | 1979-06-19 |
| ES489641A0 (es) | 1981-04-01 |
| ZA787351B (en) | 1980-08-27 |
| MW1679A1 (en) | 1981-04-08 |
| ES8400413A2 (es) | 1983-10-16 |
| JPS554389A (en) | 1980-01-12 |
| AU525698B2 (en) | 1982-11-25 |
| FR2429206B2 (de) | 1983-06-03 |
| HU184221B (en) | 1984-07-30 |
| AU4820179A (en) | 1980-03-20 |
| ZM5379A1 (en) | 1981-07-21 |
| IE48760B1 (en) | 1985-05-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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