SK286264B6 - Derivát pyrimidinylbenzimidazolu alebo triazinylbenzimidazolu, medziprodukty na jeho prípravu a poľnohospodársky/záhradnícky fungicíd s jeho obsahom - Google Patents
Derivát pyrimidinylbenzimidazolu alebo triazinylbenzimidazolu, medziprodukty na jeho prípravu a poľnohospodársky/záhradnícky fungicíd s jeho obsahom Download PDFInfo
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- SK286264B6 SK286264B6 SK615-2001A SK6152001A SK286264B6 SK 286264 B6 SK286264 B6 SK 286264B6 SK 6152001 A SK6152001 A SK 6152001A SK 286264 B6 SK286264 B6 SK 286264B6
- Authority
- SK
- Slovakia
- Prior art keywords
- ome
- alkoxy
- alkyl
- group
- oet
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- 239000000417 fungicide Substances 0.000 title claims abstract description 19
- WTZRQYJHRXQWTK-UHFFFAOYSA-N 2-pyrimidin-2-yl-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1C1=NC=CC=N1 WTZRQYJHRXQWTK-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 239000000543 intermediate Substances 0.000 title abstract description 5
- 239000004480 active ingredient Substances 0.000 claims abstract description 8
- 230000000855 fungicidal effect Effects 0.000 claims abstract description 6
- 239000000460 chlorine Substances 0.000 claims description 137
- 125000003545 alkoxy group Chemical group 0.000 claims description 104
- 125000000217 alkyl group Chemical group 0.000 claims description 91
- -1 triazin-2-yl Chemical group 0.000 claims description 74
- 150000001875 compounds Chemical class 0.000 claims description 64
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 47
- 229910052736 halogen Inorganic materials 0.000 claims description 44
- 150000002367 halogens Chemical group 0.000 claims description 42
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 42
- 125000003282 alkyl amino group Chemical group 0.000 claims description 34
- 125000005843 halogen group Chemical group 0.000 claims description 25
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 23
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 23
- 125000004414 alkyl thio group Chemical group 0.000 claims description 21
- 125000001188 haloalkyl group Chemical group 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 20
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 20
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 19
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 18
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 16
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 150000002431 hydrogen Chemical group 0.000 claims description 11
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- RSAWQCDTJIQFAD-UHFFFAOYSA-N 4-chloro-1-n-(4,6-dimethoxy-1,3,5-triazin-2-yl)benzene-1,2-diamine Chemical compound COC1=NC(OC)=NC(NC=2C(=CC(Cl)=CC=2)N)=N1 RSAWQCDTJIQFAD-UHFFFAOYSA-N 0.000 claims description 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- WGLYXMYIFDWZPR-UHFFFAOYSA-N 2-n,2-n,4-n,4-n-tetraethyl-6-n-(2-nitrophenyl)-1,3,5-triazine-2,4,6-triamine Chemical compound CCN(CC)C1=NC(N(CC)CC)=NC(NC=2C(=CC=CC=2)[N+]([O-])=O)=N1 WGLYXMYIFDWZPR-UHFFFAOYSA-N 0.000 claims description 2
- WUNIETPQNJGKFG-UHFFFAOYSA-N 4,6-dichloro-n-(2-nitrophenyl)-1,3,5-triazin-2-amine Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=NC(Cl)=NC(Cl)=N1 WUNIETPQNJGKFG-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 1
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 1
- LWPUUSTXVSSVLQ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n-tetraethyl-6-n-(4-methyl-2-nitrophenyl)-1,3,5-triazine-2,4,6-triamine Chemical compound CCN(CC)C1=NC(N(CC)CC)=NC(NC=2C(=CC(C)=CC=2)[N+]([O-])=O)=N1 LWPUUSTXVSSVLQ-UHFFFAOYSA-N 0.000 claims 1
- JNHNYVGHUQDYLS-UHFFFAOYSA-N 4,6-dichloro-n-(4-methoxy-2-nitrophenyl)-1,3,5-triazin-2-amine Chemical compound [O-][N+](=O)C1=CC(OC)=CC=C1NC1=NC(Cl)=NC(Cl)=N1 JNHNYVGHUQDYLS-UHFFFAOYSA-N 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2332
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- 210000000941 bile Anatomy 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 39
- 239000000047 product Substances 0.000 description 30
- 239000002904 solvent Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000000843 powder Substances 0.000 description 20
- 238000000034 method Methods 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 229920000728 polyester Polymers 0.000 description 12
- 238000001914 filtration Methods 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 201000010099 disease Diseases 0.000 description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 238000000605 extraction Methods 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 238000007796 conventional method Methods 0.000 description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 150000003931 anilides Chemical class 0.000 description 6
- 230000004071 biological effect Effects 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000000428 dust Substances 0.000 description 6
- 239000012442 inert solvent Substances 0.000 description 6
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000004563 wettable powder Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 230000001804 emulsifying effect Effects 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 210000003746 feather Anatomy 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- CLBDFJIIPMNCSN-UHFFFAOYSA-N n-(4-chloro-2-nitrophenyl)-4,6-dimethoxy-1,3,5-triazin-2-amine Chemical compound COC1=NC(OC)=NC(NC=2C(=CC(Cl)=CC=2)[N+]([O-])=O)=N1 CLBDFJIIPMNCSN-UHFFFAOYSA-N 0.000 description 3
- NGCURIJPLVFJJH-UHFFFAOYSA-N n-phenyltriazin-4-amine Chemical class C=1C=NN=NC=1NC1=CC=CC=C1 NGCURIJPLVFJJH-UHFFFAOYSA-N 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- YJUUZFWMKJBVFJ-UHFFFAOYSA-N 1,3-dimethylimidazolidin-4-one Chemical compound CN1CN(C)C(=O)C1 YJUUZFWMKJBVFJ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- MWPVZJJSQQLFEB-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-2-methoxybenzimidazole Chemical compound COC1=NC2=CC=CC=C2N1C1=NC(OC)=CC(OC)=N1 MWPVZJJSQQLFEB-UHFFFAOYSA-N 0.000 description 2
- IXVYXVXZJJCRFU-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-5-methylbenzimidazol-2-amine Chemical compound COC1=CC(OC)=NC(N2C3=CC=C(C)C=C3N=C2N)=N1 IXVYXVXZJJCRFU-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- UZLVRGBLDHUIDD-UHFFFAOYSA-N 2-n-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylbenzene-1,2-diamine Chemical compound COC1=NC(OC)=NC(NC=2C(=CC=C(C)C=2)N)=N1 UZLVRGBLDHUIDD-UHFFFAOYSA-N 0.000 description 2
- BTRNEFRKPPZRQA-UHFFFAOYSA-N 2-n-(4,6-dimethoxypyrimidin-2-yl)-4-methylbenzene-1,2-diamine Chemical compound COC1=CC(OC)=NC(NC=2C(=CC=C(C)C=2)N)=N1 BTRNEFRKPPZRQA-UHFFFAOYSA-N 0.000 description 2
- ITDVJJVNAASTRS-UHFFFAOYSA-N 4,6-dimethoxy-2-methylsulfonylpyrimidine Chemical compound COC1=CC(OC)=NC(S(C)(=O)=O)=N1 ITDVJJVNAASTRS-UHFFFAOYSA-N 0.000 description 2
- KXMOBKHNXKAUJD-UHFFFAOYSA-N 4,6-dimethoxy-n-(4-methyl-2-nitrophenyl)-1,3,5-triazin-2-amine Chemical compound COC1=NC(OC)=NC(NC=2C(=CC(C)=CC=2)[N+]([O-])=O)=N1 KXMOBKHNXKAUJD-UHFFFAOYSA-N 0.000 description 2
- ZWVBPETWMMFNQP-UHFFFAOYSA-N 4,6-dimethoxy-n-(4-methyl-2-nitrophenyl)pyrimidin-2-amine Chemical compound COC1=CC(OC)=NC(NC=2C(=CC(C)=CC=2)[N+]([O-])=O)=N1 ZWVBPETWMMFNQP-UHFFFAOYSA-N 0.000 description 2
- MGMBUMDYIHNZKO-UHFFFAOYSA-N 5-chloro-1-(4,6-dimethoxy-1,3,5-triazin-2-yl)-2-methylbenzimidazole Chemical compound COC1=NC(OC)=NC(N2C3=CC=C(Cl)C=C3N=C2C)=N1 MGMBUMDYIHNZKO-UHFFFAOYSA-N 0.000 description 2
- WFFZSUIFSVKWHZ-UHFFFAOYSA-N 5-chloro-1-(4,6-dimethoxy-1,3,5-triazin-2-yl)benzimidazol-2-amine Chemical compound COC1=NC(OC)=NC(N2C3=CC=C(Cl)C=C3N=C2N)=N1 WFFZSUIFSVKWHZ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- 240000008067 Cucumis sativus Species 0.000 description 2
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- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
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- 241000233866 Fungi Species 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 241001361634 Rhizoctonia 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
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000008059 anilinopyrimidines Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 150000001556 benzimidazoles Chemical class 0.000 description 2
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 235000011116 calcium hydroxide Nutrition 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
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- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
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- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
- 125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000006137 n-hexyl sulfonyl group Chemical group 0.000 description 1
- 125000004718 n-hexylthio group Chemical group C(CCCCC)S* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 208000005687 scabies Diseases 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP34361498 | 1998-11-17 | ||
| JP3956699 | 1999-02-18 | ||
| PCT/JP1999/006364 WO2000029404A1 (fr) | 1998-11-17 | 1999-11-15 | Derives de pyrimidinylbenzimidazole et de triazinylbenzimidazole et bactericides agricoles/horticoles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK6152001A3 SK6152001A3 (en) | 2001-12-03 |
| SK286264B6 true SK286264B6 (sk) | 2008-06-06 |
Family
ID=26378972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK615-2001A SK286264B6 (sk) | 1998-11-17 | 1999-11-15 | Derivát pyrimidinylbenzimidazolu alebo triazinylbenzimidazolu, medziprodukty na jeho prípravu a poľnohospodársky/záhradnícky fungicíd s jeho obsahom |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US6576631B1 (de) |
| EP (1) | EP1132387B1 (de) |
| KR (1) | KR100631307B1 (de) |
| CN (1) | CN1243002C (de) |
| AT (1) | ATE305465T1 (de) |
| AU (1) | AU755538B2 (de) |
| BR (1) | BR9915401B1 (de) |
| CA (1) | CA2350968C (de) |
| CZ (1) | CZ20011466A3 (de) |
| DE (1) | DE69927516T2 (de) |
| HU (1) | HUP0104171A3 (de) |
| IL (2) | IL143157A0 (de) |
| NZ (1) | NZ511311A (de) |
| PL (1) | PL194045B1 (de) |
| RU (1) | RU2222536C2 (de) |
| SK (1) | SK286264B6 (de) |
| TR (1) | TR200101381T2 (de) |
| WO (1) | WO2000029404A1 (de) |
Families Citing this family (370)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR038368A1 (es) * | 2002-02-01 | 2005-01-12 | Novartis Ag | Compuestos n-pirimidin-2-il-aminas sustituidas como inhibidores de ige, una composicion farmaceutica y el uso de dichos compuestos para la preparacion de un medicamento |
| CA2502970A1 (en) * | 2002-11-28 | 2004-06-10 | Schering Aktiengesellschaft | Chk-, pdk- and akt-inhibitory pyrimidines, their production and use as pharmaceutical agents |
| US20050107374A1 (en) * | 2003-10-21 | 2005-05-19 | Amgen Inc. | Substituted heterocyclic compounds and methods of use |
| CN1629157A (zh) * | 2003-12-19 | 2005-06-22 | 中国科学院上海药物研究所 | 哌嗪三嗪类化合物、其制备方法及药物组合物 |
| JP2006056871A (ja) * | 2004-07-23 | 2006-03-02 | Bayer Cropscience Ag | スルホンアニリド類の農園芸用殺菌剤としての利用 |
| JP5054004B2 (ja) * | 2005-07-01 | 2012-10-24 | アイアールエム・リミテッド・ライアビリティ・カンパニー | タンパク質キナーゼ阻害剤としてのピリミジン置換ベンゾイミダゾール誘導体 |
| NZ566021A (en) | 2005-07-26 | 2011-03-31 | Vertex Pharma | Benzimidazoles useful as inhibitors of protein kinases |
| US8239882B2 (en) * | 2005-08-30 | 2012-08-07 | Microsoft Corporation | Markup based extensibility for user interfaces |
| WO2007035309A1 (en) * | 2005-09-15 | 2007-03-29 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| SI2300013T1 (en) | 2008-05-21 | 2018-03-30 | Adriad Pharmacaceuticals, Inc. | Phosphorus derivatives as kinase inhibitors |
| US9273077B2 (en) | 2008-05-21 | 2016-03-01 | Ariad Pharmaceuticals, Inc. | Phosphorus derivatives as kinase inhibitors |
| WO2010012745A2 (en) * | 2008-07-29 | 2010-02-04 | Boehringer Ingelheim International Gmbh | Benzimidazoles |
| CA2743449C (en) | 2008-11-12 | 2016-10-18 | Ariad Pharmaceuticals, Inc. | Pyrazinopyrazines and derivatives as kinase inhibitors |
| WO2010103065A1 (en) | 2009-03-11 | 2010-09-16 | Basf Se | Fungicidal compositions and their use |
| EP2413691A2 (de) | 2009-04-02 | 2012-02-08 | Basf Se | Verfahren zur reduzierung von schädigungen in pflanzen durch sonnenverbrennung |
| CN101884329B (zh) * | 2009-05-15 | 2013-06-12 | 中国科学院化学研究所 | 一种三嗪类衍生物作为杀菌剂的用途 |
| WO2010142779A1 (en) | 2009-06-12 | 2010-12-16 | Basf Se | Antifungal 1,2,4-triazolyl derivatives having a 5- sulfur substituent |
| WO2010146032A2 (de) | 2009-06-16 | 2010-12-23 | Basf Se | Fungizide mischungen |
| CN102803231A (zh) | 2009-06-18 | 2012-11-28 | 巴斯夫欧洲公司 | 杀真菌的1，2，4-三唑衍生物 |
| JP2012530111A (ja) | 2009-06-18 | 2012-11-29 | ビーエーエスエフ ソシエタス・ヨーロピア | ５−硫黄置換基を有する抗菌類性１，２，４−トリアゾリル誘導体 |
| EP2443097A1 (de) | 2009-06-18 | 2012-04-25 | Basf Se | Antimykotische 1,2,4-triazolylderivate |
| WO2010146116A1 (en) | 2009-06-18 | 2010-12-23 | Basf Se | Triazole compounds carrying a sulfur substituent |
| CN102459241A (zh) | 2009-06-18 | 2012-05-16 | 巴斯夫欧洲公司 | 带有硫取代基的三唑化合物 |
| WO2010146115A1 (en) | 2009-06-18 | 2010-12-23 | Basf Se | Triazole compounds carrying a sulfur substituent |
| CA2764541A1 (en) | 2009-06-18 | 2010-12-23 | Basf Se | Fungicidal mixtures |
| WO2010149758A1 (en) | 2009-06-25 | 2010-12-29 | Basf Se | Antifungal 1, 2, 4-triazolyl derivatives |
| BR112012001001A2 (pt) | 2009-07-14 | 2016-11-16 | Basf Se | compositos azol das formulas i e ii, compostos das formulas i e i, compostos de formula ix, composição agricola, uso de um composto farmaceutica, metodo para tratar infecções de câncer ou virus para combater fungos zoopatigênicos ou humanopatogenicos |
| BR112012001595B1 (pt) | 2009-07-28 | 2018-06-05 | Basf Se | Composição de suspo-emulsão pesticida, método para preparar a composição de suspo-emulsão pesticida, uso de uma composição de suspo- emulsão, métodos para combater fungos fitopatogênicos e método para tratar sementes |
| WO2011026796A1 (en) | 2009-09-01 | 2011-03-10 | Basf Se | Synergistic fungicidal mixtures comprising lactylates and method for combating phytopathogenic fungi |
| US8242284B1 (en) * | 2009-09-21 | 2012-08-14 | The United States Of America As Represented By The United States Department Of Energy | Anti-cancer agents based on 6-trifluoromethoxybenzimidazole derivatives and method of making |
| WO2011069912A1 (de) | 2009-12-07 | 2011-06-16 | Basf Se | Triazolverbindungen, ihre verwendung sowie sie enthaltende mittel |
| WO2011069916A1 (de) | 2009-12-08 | 2011-06-16 | Basf Se | Triazolverbindungen, ihre verwendung als fungizide sowie sie enthaltende mittel |
| WO2011069894A1 (de) | 2009-12-08 | 2011-06-16 | Basf Se | Triazolverbindungen, ihre verwendung sowie sie enthaltende mittel |
| WO2011110583A2 (en) | 2010-03-10 | 2011-09-15 | Basf Se | Fungicidal mixtures comprising triazole derivatives |
| BR112012023500B8 (pt) | 2010-03-18 | 2018-05-22 | Basf Se | composição sinérgica, método para controlar fungos nocivos fitopatogênicos e método para proteger o material de propagação de planta de fungos patogênicos de planta |
| EP2366289A1 (de) | 2010-03-18 | 2011-09-21 | Basf Se | Synergistische fungizide Mischungen |
| DE102011017669A1 (de) | 2010-04-29 | 2011-11-03 | Basf Se | Synergistische fungizide Mischungen |
| DE102011017541A1 (de) | 2010-04-29 | 2011-11-10 | Basf Se | Synergistische fungizide Mischungen |
| DE102011017716A1 (de) | 2010-04-29 | 2011-11-03 | Basf Se | Synergistische fungizide Mischungen |
| DE102011017670A1 (de) | 2010-04-29 | 2011-11-03 | Basf Se | Synergistische fungizide Mischungen |
| DE102011017715A1 (de) | 2010-04-29 | 2012-03-08 | Basf Se | Synergistische fungizide Mischungen |
| EP2401915A1 (de) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazolopyridin-Verbindungen |
| EP2402340A1 (de) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazolopyridin-Verbindungen |
| EP2402338A1 (de) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazolopyridin-Verbindungen |
| EP2402344A1 (de) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazolkondensierte bicyclische Verbindungen |
| EP2402339A1 (de) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazolopyridin-Verbindungen |
| EP2402337A1 (de) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazolopyridin-Verbindungen |
| EP2402343A1 (de) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazole kondensierte bizyclische Verbindungen |
| EP2402345A1 (de) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazole kondensierte bizyclische Verbindungen |
| EP2402336A1 (de) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazolopyridin-Verbindungen |
| EP2402335A1 (de) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazolopyridin-Verbindungen |
| WO2012016989A2 (en) | 2010-08-03 | 2012-02-09 | Basf Se | Fungicidal compositions |
| EP2447262A1 (de) | 2010-10-29 | 2012-05-02 | Basf Se | Pyrrol-, Furan- und Thiopen-Derivate und ihre Verwendung als Fungizide |
| EP2447261A1 (de) | 2010-10-29 | 2012-05-02 | Basf Se | Pyrrol-, Furan- und Thiophenderivate und ihre Verwendung als Fungizide |
| WO2012077061A1 (en) | 2010-12-08 | 2012-06-14 | Basf Se | Pesticidal mixtures |
| EP2465350A1 (de) | 2010-12-15 | 2012-06-20 | Basf Se | Pestizidgemische |
| EP2481284A3 (de) | 2011-01-27 | 2012-10-17 | Basf Se | Pestizidgemische |
| JP6049684B2 (ja) | 2011-03-23 | 2016-12-21 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | イミダゾリウム基を含むポリマーのイオン性化合物を含有する組成物 |
| JP2014516356A (ja) | 2011-04-15 | 2014-07-10 | ビーエーエスエフ ソシエタス・ヨーロピア | 植物病原性菌類を駆除するための置換されたジチイン−テトラカルボキシイミドの使用 |
| US9137997B2 (en) | 2011-04-15 | 2015-09-22 | Basf Se | Use of substituted dithiine-dicarboximides for combating phytopathogenic fungi |
| CN103491775A (zh) | 2011-04-21 | 2014-01-01 | 巴斯夫欧洲公司 | 3,4-二取代的吡咯-2,5-二酮及其作为杀真菌剂的用途 |
| EP2704572B1 (de) | 2011-05-04 | 2015-12-30 | Ariad Pharmaceuticals, Inc. | Verfahren zur hemmung der zellproliferation bei efgr-vermitteltem krebs |
| BR112013030476A2 (pt) | 2011-06-17 | 2017-06-20 | Basf Se | mistura, composição agroquímica, método para controlar fungos nocivos fitopatogênicos e material de propagação de planta |
| MY163323A (en) | 2011-07-13 | 2017-09-15 | Basf Agro Bv | Fungicidal substituted 2-[2-halogenalkyl-4-(phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds |
| CN103814017A (zh) | 2011-07-15 | 2014-05-21 | 巴斯夫欧洲公司 | 杀真菌的苯基烷基取代的2-[2-氯-4-(4-氯苯氧基)苯基]-1-[1,2,4]三唑-1-基乙醇化合物 |
| WO2013010885A1 (en) | 2011-07-15 | 2013-01-24 | Basf Se | Fungicidal alkyl- and aryl-substituted 2-[2-chloro-4-(dihalo-phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds |
| PE20140837A1 (es) | 2011-07-15 | 2014-07-10 | Basf Se | Compuestos fungicidas 2-[2-cloro-4-(4-cloro-fenoxi)-fenil]-1-[1,2,4]triazol-1-il-etanol alquilo sustituidos |
| MX2014001671A (es) | 2011-08-15 | 2014-05-27 | Basf Se | Compuestos fungicidas de 1-{2-[2-halo-4-(4-halogen-fenoxi)-fenil]- 2-aluiniloxi-etil}-1h[1,2,4]triazol sustituidos. |
| EP2559688A1 (de) | 2011-08-15 | 2013-02-20 | Basf Se | Fungizide substituierte 1-{2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-2-butoxy-ethyl}-1h [1,2,4]triazol-Verbindungen |
| EP2744789A1 (de) | 2011-08-15 | 2014-06-25 | Basf Se | Fungizide substituierte 1-{2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-2-alkoxy-hexyl}-1h [1,2,4]triazol-verbindungen |
| BR112014003412A2 (pt) | 2011-08-15 | 2017-03-14 | Basf Se | compostos de fórmula i, processo, compostos de fórmula xii, viii e xi, composições agroquímicas, utilização e semente revestida |
| EA201400232A1 (ru) | 2011-08-15 | 2014-07-30 | Басф Се | Фунгицидные замещенные 1-{2-[2-галоген-4-(4-галогенфенокси)фенил]-2-алкокси-2-циклилэтил}-1н-[1,2,4]триазольные соединения |
| US20140162876A1 (en) | 2011-08-15 | 2014-06-12 | Basf Se | Fungicidal substituted 1--1H-[1,2,4]triazole compounds |
| EP2744791B1 (de) | 2011-08-15 | 2015-10-28 | Basf Se | Fungizide substituierte 1-{2-[2-halo-4-(4-halogen-phenoxy-)phenyl-]2-alkoxy-3-methyl-butyl}-1h-[1,2,4-]triazol-verbindungen |
| EP2744790B1 (de) | 2011-08-15 | 2016-04-27 | Basf Se | Fungizide substituierte 1-{2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-2-alkoxy-2-alkynyl-ethyl}-1h [1,2,4]triazol-verbindungen |
| LT3329919T (lt) | 2011-11-11 | 2020-02-10 | Gilead Apollo, Llc | Acc inhibitoriai ir jų panaudojimas |
| US9271501B2 (en) | 2011-12-21 | 2016-03-01 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi resistant to QO inhibitors |
| WO2013113781A1 (en) | 2012-02-03 | 2013-08-08 | Basf Se | Fungicidal pyrimidine compounds i |
| WO2013113720A1 (en) | 2012-02-03 | 2013-08-08 | Basf Se | Fungicidal pyrimidine compounds |
| WO2013113716A1 (en) | 2012-02-03 | 2013-08-08 | Basf Se | Fungicidal pyrimidine compounds |
| WO2013113788A1 (en) | 2012-02-03 | 2013-08-08 | Basf Se | Fungicidal pyrimidine compounds |
| WO2013113773A1 (en) | 2012-02-03 | 2013-08-08 | Basf Se | Fungicidal pyrimidine compounds |
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1999
- 1999-11-15 AT AT99972212T patent/ATE305465T1/de not_active IP Right Cessation
- 1999-11-15 US US09/830,578 patent/US6576631B1/en not_active Expired - Fee Related
- 1999-11-15 CA CA002350968A patent/CA2350968C/en not_active Expired - Fee Related
- 1999-11-15 WO PCT/JP1999/006364 patent/WO2000029404A1/ja active IP Right Grant
- 1999-11-15 NZ NZ511311A patent/NZ511311A/xx not_active IP Right Cessation
- 1999-11-15 EP EP99972212A patent/EP1132387B1/de not_active Expired - Lifetime
- 1999-11-15 RU RU2001116600/04A patent/RU2222536C2/ru not_active IP Right Cessation
- 1999-11-15 KR KR1020017005888A patent/KR100631307B1/ko not_active IP Right Cessation
- 1999-11-15 CZ CZ20011466A patent/CZ20011466A3/cs unknown
- 1999-11-15 DE DE69927516T patent/DE69927516T2/de not_active Expired - Lifetime
- 1999-11-15 IL IL14315799A patent/IL143157A0/xx unknown
- 1999-11-15 BR BRPI9915401-3A patent/BR9915401B1/pt not_active IP Right Cessation
- 1999-11-15 AU AU11805/00A patent/AU755538B2/en not_active Ceased
- 1999-11-15 PL PL99347688A patent/PL194045B1/pl not_active IP Right Cessation
- 1999-11-15 CN CNB998154881A patent/CN1243002C/zh not_active Expired - Fee Related
- 1999-11-15 TR TR2001/01381T patent/TR200101381T2/xx unknown
- 1999-11-15 HU HU0104171A patent/HUP0104171A3/hu unknown
- 1999-11-15 SK SK615-2001A patent/SK286264B6/sk not_active IP Right Cessation
-
2001
- 2001-05-15 IL IL143157A patent/IL143157A/en not_active IP Right Cessation
-
2003
- 2003-03-10 US US10/383,693 patent/US6872729B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| BR9915401B1 (pt) | 2011-04-19 |
| EP1132387A1 (de) | 2001-09-12 |
| PL194045B1 (pl) | 2007-04-30 |
| HUP0104171A3 (en) | 2002-04-29 |
| CZ20011466A3 (cs) | 2001-09-12 |
| SK6152001A3 (en) | 2001-12-03 |
| TR200101381T2 (tr) | 2002-05-21 |
| AU755538B2 (en) | 2002-12-12 |
| WO2000029404A1 (fr) | 2000-05-25 |
| AU1180500A (en) | 2000-06-05 |
| CN1333768A (zh) | 2002-01-30 |
| US6576631B1 (en) | 2003-06-10 |
| PL347688A1 (en) | 2002-04-22 |
| KR100631307B1 (ko) | 2006-10-04 |
| HUP0104171A2 (hu) | 2002-02-28 |
| BR9915401A (pt) | 2001-08-14 |
| CA2350968C (en) | 2008-10-28 |
| IL143157A0 (en) | 2002-04-21 |
| DE69927516T2 (de) | 2006-03-16 |
| US20040023966A1 (en) | 2004-02-05 |
| KR20010080976A (ko) | 2001-08-25 |
| US6872729B2 (en) | 2005-03-29 |
| DE69927516D1 (de) | 2006-02-09 |
| IL143157A (en) | 2010-11-30 |
| RU2222536C2 (ru) | 2004-01-27 |
| NZ511311A (en) | 2002-10-25 |
| EP1132387A4 (de) | 2002-06-05 |
| CN1243002C (zh) | 2006-02-22 |
| WO2000029404A8 (fr) | 2000-09-08 |
| ATE305465T1 (de) | 2005-10-15 |
| CA2350968A1 (en) | 2000-05-25 |
| EP1132387B1 (de) | 2005-09-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20111115 |