EA006710B1 - ПРОИЗВОДНЫЕ 5-АМИНО-6-ФЕНИЛ-7-ГАЛОГЕН[1,2,4]ТРИАЗОЛО[1,5-a]ПИРИМИДИНА - Google Patents
ПРОИЗВОДНЫЕ 5-АМИНО-6-ФЕНИЛ-7-ГАЛОГЕН[1,2,4]ТРИАЗОЛО[1,5-a]ПИРИМИДИНА Download PDFInfo
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- EA006710B1 EA006710B1 EA200301105A EA200301105A EA006710B1 EA 006710 B1 EA006710 B1 EA 006710B1 EA 200301105 A EA200301105 A EA 200301105A EA 200301105 A EA200301105 A EA 200301105A EA 006710 B1 EA006710 B1 EA 006710B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- formula
- compounds
- alkyl
- halogen
- hydrogen
- Prior art date
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- 239000000417 fungicide Substances 0.000 title description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
- 239000001257 hydrogen Substances 0.000 claims abstract description 30
- 239000000203 mixture Substances 0.000 claims abstract description 24
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 19
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 15
- 241000233866 Fungi Species 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 230000003032 phytopathogenic effect Effects 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 7
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 4
- SRNKZYRMFBGSGE-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyrimidine Chemical class N1=CC=CN2N=CN=C21 SRNKZYRMFBGSGE-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract 2
- 125000004991 fluoroalkenyl group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 78
- -1 nitro, hydroxyl Chemical group 0.000 claims description 42
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 25
- 229910052731 fluorine Inorganic materials 0.000 claims description 25
- 239000011737 fluorine Substances 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims description 3
- 230000003993 interaction Effects 0.000 claims description 3
- 239000002689 soil Substances 0.000 claims description 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 230000001079 digestive effect Effects 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 8
- 125000001188 haloalkyl group Chemical group 0.000 abstract description 5
- 125000005843 halogen group Chemical group 0.000 abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- 125000000304 alkynyl group Chemical group 0.000 abstract description 2
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 1
- 239000013256 coordination polymer Substances 0.000 description 50
- 241000196324 Embryophyta Species 0.000 description 38
- 239000013543 active substance Substances 0.000 description 22
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 20
- 239000004480 active ingredient Substances 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 230000000855 fungicidal effect Effects 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 239000003995 emulsifying agent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000007900 aqueous suspension Substances 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 8
- 241000894007 species Species 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 6
- 240000007594 Oryza sativa Species 0.000 description 5
- 235000007164 Oryza sativa Nutrition 0.000 description 5
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- 238000010410 dusting Methods 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
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- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000012086 standard solution Substances 0.000 description 5
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
- 244000070406 Malus silvestris Species 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 240000003768 Solanum lycopersicum Species 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 230000002538 fungal effect Effects 0.000 description 4
- 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 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 235000013311 vegetables Nutrition 0.000 description 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 3
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical class CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 3
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical class COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 3
- 244000105624 Arachis hypogaea Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 235000011430 Malus pumila Nutrition 0.000 description 3
- 235000015103 Malus silvestris Nutrition 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 244000098338 Triticum aestivum Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
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- 150000002790 naphthalenes Chemical class 0.000 description 3
- 235000020232 peanut Nutrition 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 2
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 2
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- 239000005995 Aluminium silicate Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000000832 Ayote Nutrition 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- 240000008067 Cucumis sativus Species 0.000 description 2
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- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000221785 Erysiphales Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 244000299507 Gossypium hirsutum Species 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
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- 150000001298 alcohols Chemical class 0.000 description 2
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- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 2
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- 125000004429 atom Chemical group 0.000 description 2
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Chemical group 0.000 description 2
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 1
- DPGXTUOZQHBZRC-UHFFFAOYSA-N 1-[2-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-yl]ethyl]-1,2,4-triazole Chemical compound O1C(CC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CCN1N=CN=C1 DPGXTUOZQHBZRC-UHFFFAOYSA-N 0.000 description 1
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- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
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- 125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AMEKQAFGQBKLKX-UHFFFAOYSA-N oxycarboxin Chemical compound O=S1(=O)CCOC(C)=C1C(=O)NC1=CC=CC=C1 AMEKQAFGQBKLKX-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 150000008060 phenylpyrroles Chemical class 0.000 description 1
- MTZWHHIREPJPTG-UHFFFAOYSA-N phorone Chemical compound CC(C)=CC(=O)C=C(C)C MTZWHHIREPJPTG-UHFFFAOYSA-N 0.000 description 1
- FUWGSUOSJRCEIV-UHFFFAOYSA-N phosphonothioic O,O-acid Chemical compound OP(O)=S FUWGSUOSJRCEIV-UHFFFAOYSA-N 0.000 description 1
- IBSNKSODLGJUMQ-SDNWHVSQSA-N picoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-SDNWHVSQSA-N 0.000 description 1
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000002641 tar oil Substances 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical group BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01109011 | 2001-04-11 | ||
| PCT/EP2002/003829 WO2002083676A1 (en) | 2001-04-11 | 2002-04-06 | 5-halogen-6-phenyl-7-fluoralkylamino-triazolopyrimidines as fungicides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200301105A1 EA200301105A1 (ru) | 2004-02-26 |
| EA006710B1 true EA006710B1 (ru) | 2006-02-24 |
Family
ID=8177112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200301105A EA006710B1 (ru) | 2001-04-11 | 2002-04-06 | ПРОИЗВОДНЫЕ 5-АМИНО-6-ФЕНИЛ-7-ГАЛОГЕН[1,2,4]ТРИАЗОЛО[1,5-a]ПИРИМИДИНА |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US7105664B2 (enExample) |
| EP (1) | EP1381609B1 (enExample) |
| JP (1) | JP2004531527A (enExample) |
| KR (1) | KR20030087073A (enExample) |
| CN (1) | CN1257904C (enExample) |
| AR (1) | AR035823A1 (enExample) |
| AT (1) | ATE287405T1 (enExample) |
| AU (1) | AU2002257757B2 (enExample) |
| BG (1) | BG108238A (enExample) |
| BR (1) | BR0208756A (enExample) |
| CA (1) | CA2443696A1 (enExample) |
| CZ (1) | CZ295558B6 (enExample) |
| DE (1) | DE60202672T2 (enExample) |
| EA (1) | EA006710B1 (enExample) |
| EE (1) | EE200300499A (enExample) |
| ES (1) | ES2236509T3 (enExample) |
| HU (1) | HUP0401092A3 (enExample) |
| IL (1) | IL158218A0 (enExample) |
| MX (1) | MXPA03009002A (enExample) |
| NZ (1) | NZ528745A (enExample) |
| PL (1) | PL367107A1 (enExample) |
| PT (1) | PT1381609E (enExample) |
| SK (1) | SK12522003A3 (enExample) |
| TW (1) | TWI275590B (enExample) |
| UA (1) | UA74069C2 (enExample) |
| WO (1) | WO2002083676A1 (enExample) |
| ZA (1) | ZA200307888B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6255309B1 (en) * | 1999-03-19 | 2001-07-03 | American Cyanomid Co. | Fungicidal trifluoromethylalkylamino-triazolopyrimidines |
| DE10124208A1 (de) * | 2001-05-18 | 2002-11-21 | Bayer Ag | Verwendung von Triazolopyrimidin-Derivaten als Mikrobizide |
| UA80304C2 (en) * | 2002-11-07 | 2007-09-10 | Basf Ag | Substituted 6-(2-halogenphenyl)triazolopyrimidines |
| ATE339421T1 (de) * | 2002-11-07 | 2006-10-15 | Basf Ag | 5-alkyl-7-aminotriazolopyrimidine,verfahren und zwischenprodukte zu ihrer herstellung ,sie enthaltende mittel sowie ihre verwendung zur bekämpfung von schadpilzen |
| MXPA05004369A (es) * | 2002-11-15 | 2005-07-05 | Basf Ag | Mezclas fungicidas. |
| GB0230020D0 (en) * | 2002-12-23 | 2003-01-29 | Syngenta Ltd | Fungicides |
| GB0230018D0 (en) * | 2002-12-23 | 2003-01-29 | Syngenta Ltd | Fungicides |
| EP1611135A1 (de) * | 2003-03-31 | 2006-01-04 | Basf Aktiengesellschaft | 7-alkenylamino-triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bek mpfung von schadpilzen sowie sie enthaltende mittel |
| EP1613633A1 (de) * | 2003-04-02 | 2006-01-11 | Basf Aktiengesellschaft | 7-alkinylamino-triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel |
| US7419982B2 (en) | 2003-09-24 | 2008-09-02 | Wyeth Holdings Corporation | Crystalline forms of 5-chloro-6-{2,6-difluoro-4-[3-(methylamino)propoxy]phenyl}-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine salts |
| WO2005030775A1 (en) | 2003-09-24 | 2005-04-07 | Wyeth Holdings Corporation | 6-[(substituted)phenyl]triazolopyrimidines as anticancer agents |
| CN100486580C (zh) | 2003-09-24 | 2009-05-13 | 惠氏控股公司 | 作为抗癌剂的6-芳基-7-卤基-咪唑并[1,2-a]嘧啶 |
| EP1758457A1 (de) * | 2004-06-09 | 2007-03-07 | Basf Aktiengesellschaft | Triazolopyrimidin-verbindungen und ihre verwendung zur bekämpfung von schadpilzen |
| US20080032889A1 (en) * | 2004-06-22 | 2008-02-07 | Basf Aktiengesellschaft | 6-(2-Fluorophenyl)-Triazolopyrimidines, Method For The Production Thereof, Use Thereof For Controlling Harmful Fungi, And Agents Containing The Same |
| EP1920654A1 (en) | 2006-09-13 | 2008-05-14 | Syngeta Participations AG | Novel pyridopyrazine N-oxides |
| EP1952691A3 (en) * | 2007-01-31 | 2008-09-17 | Basf Se | Method for improving plant health by application of a triazolopyrimidine derivative |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3130633A1 (de) | 1981-08-01 | 1983-02-17 | Basf Ag, 6700 Ludwigshafen | 7-amino-azolo(1,5-a)pyrimidine und diese enthaltende fungizide |
| TW224044B (enExample) | 1991-12-30 | 1994-05-21 | Shell Internat Res Schappej B V | |
| TW460476B (en) * | 1997-04-14 | 2001-10-21 | American Cyanamid Co | Fungicidal trifluoromethylalkylamino-triazolopyrimidines |
| TWI252231B (en) | 1997-04-14 | 2006-04-01 | American Cyanamid Co | Fungicidal trifluorophenyl-triazolopyrimidines |
| CA2413802A1 (en) * | 2000-06-30 | 2002-01-10 | Mark R. Schmitt | Substituted-triazolopyrimidines as anticancer agents |
-
2002
- 2002-04-06 PT PT02727533T patent/PT1381609E/pt unknown
- 2002-04-06 CZ CZ20032721A patent/CZ295558B6/cs not_active IP Right Cessation
- 2002-04-06 BR BR0208756-1A patent/BR0208756A/pt not_active IP Right Cessation
- 2002-04-06 CA CA002443696A patent/CA2443696A1/en not_active Abandoned
- 2002-04-06 IL IL15821802A patent/IL158218A0/xx unknown
- 2002-04-06 HU HU0401092A patent/HUP0401092A3/hu unknown
- 2002-04-06 CN CNB028080807A patent/CN1257904C/zh not_active Expired - Fee Related
- 2002-04-06 EA EA200301105A patent/EA006710B1/ru not_active IP Right Cessation
- 2002-04-06 DE DE60202672T patent/DE60202672T2/de not_active Expired - Fee Related
- 2002-04-06 US US10/474,460 patent/US7105664B2/en not_active Expired - Fee Related
- 2002-04-06 NZ NZ528745A patent/NZ528745A/en unknown
- 2002-04-06 ES ES02727533T patent/ES2236509T3/es not_active Expired - Lifetime
- 2002-04-06 MX MXPA03009002A patent/MXPA03009002A/es active IP Right Grant
- 2002-04-06 EE EEP200300499A patent/EE200300499A/xx unknown
- 2002-04-06 EP EP02727533A patent/EP1381609B1/en not_active Expired - Lifetime
- 2002-04-06 KR KR10-2003-7013281A patent/KR20030087073A/ko not_active Abandoned
- 2002-04-06 SK SK1252-2003A patent/SK12522003A3/sk unknown
- 2002-04-06 JP JP2002581431A patent/JP2004531527A/ja not_active Withdrawn
- 2002-04-06 PL PL02367107A patent/PL367107A1/xx not_active Application Discontinuation
- 2002-04-06 WO PCT/EP2002/003829 patent/WO2002083676A1/en not_active Ceased
- 2002-04-06 AT AT02727533T patent/ATE287405T1/de not_active IP Right Cessation
- 2002-04-06 AU AU2002257757A patent/AU2002257757B2/en not_active Ceased
- 2002-04-11 AR ARP020101339A patent/AR035823A1/es not_active Application Discontinuation
- 2002-04-11 TW TW091107358A patent/TWI275590B/zh not_active IP Right Cessation
- 2002-06-04 UA UA20031110122A patent/UA74069C2/uk unknown
-
2003
- 2003-10-07 BG BG108238A patent/BG108238A/bg unknown
- 2003-10-09 ZA ZA200307888A patent/ZA200307888B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE287405T1 (de) | 2005-02-15 |
| HUP0401092A3 (en) | 2005-10-28 |
| WO2002083676A1 (en) | 2002-10-24 |
| TWI275590B (en) | 2007-03-11 |
| PT1381609E (pt) | 2005-05-31 |
| EA200301105A1 (ru) | 2004-02-26 |
| NZ528745A (en) | 2005-03-24 |
| US20040127509A1 (en) | 2004-07-01 |
| DE60202672D1 (de) | 2005-02-24 |
| MXPA03009002A (es) | 2004-02-12 |
| JP2004531527A (ja) | 2004-10-14 |
| CN1501936A (zh) | 2004-06-02 |
| US7105664B2 (en) | 2006-09-12 |
| CZ20032721A3 (cs) | 2004-01-14 |
| EE200300499A (et) | 2003-12-15 |
| BG108238A (bg) | 2005-04-30 |
| KR20030087073A (ko) | 2003-11-12 |
| HUP0401092A2 (hu) | 2004-09-28 |
| DE60202672T2 (de) | 2005-06-16 |
| UA74069C2 (en) | 2005-10-17 |
| CA2443696A1 (en) | 2002-10-24 |
| PL367107A1 (en) | 2005-02-21 |
| CZ295558B6 (cs) | 2005-08-17 |
| BR0208756A (pt) | 2004-05-11 |
| ES2236509T3 (es) | 2005-07-16 |
| EP1381609A1 (en) | 2004-01-21 |
| IL158218A0 (en) | 2004-05-12 |
| ZA200307888B (en) | 2004-10-11 |
| SK12522003A3 (sk) | 2004-05-04 |
| AR035823A1 (es) | 2004-07-14 |
| AU2002257757B2 (en) | 2008-05-08 |
| EP1381609B1 (en) | 2005-01-19 |
| CN1257904C (zh) | 2006-05-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM AZ BY KZ KG MD TJ TM |
|
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): RU |