PL171579B1 - Srodek grzybobójczy PL - Google Patents
Srodek grzybobójczy PLInfo
- Publication number
- PL171579B1 PL171579B1 PL92312883A PL31288392A PL171579B1 PL 171579 B1 PL171579 B1 PL 171579B1 PL 92312883 A PL92312883 A PL 92312883A PL 31288392 A PL31288392 A PL 31288392A PL 171579 B1 PL171579 B1 PL 171579B1
- Authority
- PL
- Poland
- Prior art keywords
- phenyl
- hydrogen
- group
- cyclopentyl
- plants
- Prior art date
Links
- 230000000855 fungicidal effect Effects 0.000 title claims description 16
- 238000000034 method Methods 0.000 title abstract description 10
- 239000000417 fungicide Substances 0.000 title description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title description 3
- 150000003852 triazoles Chemical class 0.000 title 2
- 239000000460 chlorine Substances 0.000 claims abstract description 90
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 4
- -1 cyano, hydroxy Chemical group 0.000 claims description 114
- 150000001875 compounds Chemical class 0.000 claims description 86
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 63
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 239000004305 biphenyl Chemical group 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000004799 bromophenyl group Chemical group 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 claims description 2
- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000001680 trimethoxyphenyl group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 8
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 abstract description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract description 2
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 66
- 241000196324 Embryophyta Species 0.000 description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000007921 spray Substances 0.000 description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000002904 solvent Substances 0.000 description 16
- 230000000694 effects Effects 0.000 description 15
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 14
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- 238000005507 spraying Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000000338 in vitro Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000007900 aqueous suspension Substances 0.000 description 10
- 201000010099 disease Diseases 0.000 description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 241000233866 Fungi Species 0.000 description 9
- 240000003768 Solanum lycopersicum Species 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 241000209140 Triticum Species 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 7
- 235000021307 Triticum Nutrition 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 238000011081 inoculation Methods 0.000 description 7
- 230000001681 protective effect Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000123650 Botrytis cinerea Species 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229920001213 Polysorbate 20 Polymers 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000012634 fragment Substances 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 6
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 6
- 239000001965 potato dextrose agar Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 229920001817 Agar Polymers 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 240000005979 Hordeum vulgare Species 0.000 description 5
- 235000007340 Hordeum vulgare Nutrition 0.000 description 5
- 241000813090 Rhizoctonia solani Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 241000228452 Venturia inaequalis Species 0.000 description 5
- 239000008272 agar Substances 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 241000220225 Malus Species 0.000 description 4
- 241001668536 Oculimacula yallundae Species 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 240000006677 Vicia faba Species 0.000 description 4
- 240000006365 Vitis vinifera Species 0.000 description 4
- 235000014787 Vitis vinifera Nutrition 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000002054 inoculum Substances 0.000 description 4
- 230000003902 lesion Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 230000028070 sporulation Effects 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000221785 Erysiphales Species 0.000 description 3
- 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 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 241001281803 Plasmopara viticola Species 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000006184 cosolvent Substances 0.000 description 3
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 3
- 235000021186 dishes Nutrition 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000012025 fluorinating agent Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
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- 125000005843 halogen group Chemical group 0.000 description 3
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- 239000012044 organic layer Substances 0.000 description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
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- 150000003512 tertiary amines Chemical class 0.000 description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- MLJGYTHPCYWWAM-UHFFFAOYSA-N 5-chloro-n-cyclopentyl-6-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=CC(OC)=CC=C1C1=C(NC2CCCC2)N2N=CN=C2N=C1Cl MLJGYTHPCYWWAM-UHFFFAOYSA-N 0.000 description 2
- 241000213004 Alternaria solani Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
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- 241001330975 Magnaporthe oryzae Species 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 241000736122 Parastagonospora nodorum Species 0.000 description 2
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- 235000002098 Vicia faba var. major Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 150000001602 bicycloalkyls Chemical group 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
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- 238000005260 corrosion Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 239000008121 dextrose Substances 0.000 description 2
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- 238000003818 flash chromatography Methods 0.000 description 2
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- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
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- 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
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 235000012243 magnesium silicates Nutrition 0.000 description 1
- 239000008268 mayonnaise Substances 0.000 description 1
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- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- ISQMUWYJZWJGHB-UHFFFAOYSA-N n-cyclopentyl-6-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=CC(OC)=CC=C1C1=C(NC2CCCC2)N2N=CN=C2N=C1 ISQMUWYJZWJGHB-UHFFFAOYSA-N 0.000 description 1
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- 150000004760 silicates Chemical class 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
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- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
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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
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP91122422 | 1991-12-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL171579B1 true PL171579B1 (pl) | 1997-05-30 |
Family
ID=8207489
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL92312883A PL171579B1 (pl) | 1991-12-30 | 1992-12-28 | Srodek grzybobójczy PL |
| PL92297160A PL174047B1 (pl) | 1991-12-30 | 1992-12-28 | Sposób wytwarzania pochodnych triazolopirymidyny |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL92297160A PL174047B1 (pl) | 1991-12-30 | 1992-12-28 | Sposób wytwarzania pochodnych triazolopirymidyny |
Country Status (21)
| Country | Link |
|---|---|
| EP (2) | EP0550113B1 (env) |
| JP (1) | JP3347170B2 (env) |
| KR (1) | KR100271913B1 (env) |
| CN (2) | CN1033643C (env) |
| AT (2) | ATE192154T1 (env) |
| AU (1) | AU667204B2 (env) |
| BR (1) | BR9205172A (env) |
| CA (1) | CA2086404C (env) |
| DE (2) | DE69230977T2 (env) |
| DK (2) | DK0782997T3 (env) |
| ES (2) | ES2108727T3 (env) |
| GR (2) | GR3025920T3 (env) |
| HU (1) | HU217349B (env) |
| IL (1) | IL104244A (env) |
| NZ (1) | NZ245581A (env) |
| PL (2) | PL171579B1 (env) |
| PT (1) | PT782997E (env) |
| RU (1) | RU2089552C1 (env) |
| SG (1) | SG47563A1 (env) |
| TW (1) | TW224044B (env) |
| ZA (1) | ZA9210043B (env) |
Families Citing this family (72)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5593996A (en) * | 1991-12-30 | 1997-01-14 | American Cyanamid Company | Triazolopyrimidine derivatives |
| IL108731A (en) * | 1993-03-04 | 1997-03-18 | Shell Int Research | 6, N-DISUBSTITUTED-£1, 2, 4| TRIAZOLO-£1, 5-a| PYRIMIDINE- 7-AMINE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS FUNGICIDES |
| IL108747A (en) * | 1993-03-04 | 1999-03-12 | Shell Int Research | Mushroom-killing preparations containing a history of 6 metamorphoses of 5 - 7 Dihalo - 1, 2 - 4 Triazlo [A-1,5] Pyrimidine Certain such new compounds and their preparation |
| US5869486A (en) * | 1995-02-24 | 1999-02-09 | Ono Pharmaceutical Co., Ltd. | Fused pyrimidines and pyriazines as pharmaceutical compounds |
| RU2147584C1 (ru) | 1995-10-27 | 2000-04-20 | Американ Цианамид Компани | Способ получения дигалоидазолопиримидинов и способ получения дигидроксиазолопиримидинов |
| US5817663A (en) * | 1996-10-07 | 1998-10-06 | American Cyanamid Company | Pentafluorophenylazolopyrimidines |
| US5750766A (en) * | 1997-03-18 | 1998-05-12 | American Cyanamid Company | Process for the preparation of arylmalonates |
| US5756815A (en) * | 1997-03-18 | 1998-05-26 | American Cyanamid Company | Process for the preparation arylamalonates |
| US6117876A (en) * | 1997-04-14 | 2000-09-12 | American Cyanamid Company | Fungicidal trifluorophenyl-triazolopyrimidines |
| TW460476B (en) * | 1997-04-14 | 2001-10-21 | American Cyanamid Co | Fungicidal trifluoromethylalkylamino-triazolopyrimidines |
| NZ506247A (en) * | 1998-02-11 | 2003-03-28 | American Cyanamid Co | Fungicidal 7-(alkyl, alkenyl, alkadienyl, cycloalkyl, cycloalkenyl or aryl)-[1,2,4]triazolo[1,5-a]pyrimidines |
| JPH11322517A (ja) * | 1998-03-17 | 1999-11-24 | American Cyanamid Co | トリアゾロピリミジン類の効力の増進 |
| US6124301A (en) * | 1998-03-17 | 2000-09-26 | American Cyanamid Company | Enhancement of the efficacy of triazolopyrimidines |
| US6284762B1 (en) * | 1998-03-23 | 2001-09-04 | American Cyanamid Company | Fungicidal 6-(2-halo-4-alkoxyphenyl)-triazolopyrimidines |
| PE20001145A1 (es) * | 1998-09-10 | 2000-10-25 | American Cyanamid Co | Mezclas fungicidas |
| US5986135A (en) * | 1998-09-25 | 1999-11-16 | American Cyanamid Company | Fungicidal trifluoromethylalkylamino-triazolopyrimidines |
| US6277856B1 (en) * | 1998-09-25 | 2001-08-21 | American Cynamid Co. | Fungicidal mixtures |
| US6242451B1 (en) * | 1998-09-25 | 2001-06-05 | Klaus-Juergen Pees | Fungicidal trihalophenyl-triazolopyrimidines |
| JP2000103790A (ja) * | 1998-09-25 | 2000-04-11 | American Cyanamid Co | 殺菌・殺カビ性のトリハロフェニル―トリアゾロピリミジン類 |
| TWI229674B (en) * | 1998-12-04 | 2005-03-21 | Astra Pharma Prod | Novel triazolo[4,5-d]pyrimidine compounds, pharmaceutical composition containing the same, their process for preparation and uses |
| CN1320880C (zh) * | 1998-12-23 | 2007-06-13 | 伊迪亚股份公司 | 改进的体内局部无创伤用制剂 |
| US6699874B2 (en) | 1999-09-24 | 2004-03-02 | Basf Aktiengesellschaft | Fungicidal mixtures |
| GB2355261A (en) * | 1999-10-13 | 2001-04-18 | American Cyanamid Co | Triazolopyrimidine fungicides |
| US6559151B2 (en) | 2000-05-08 | 2003-05-06 | Basf Aktiengesellschaft | 6-(2-trifluoromethyl-phenyl)-triazolopyrimidines |
| DE60116092T2 (de) * | 2000-06-13 | 2006-07-06 | Basf Ag | Fungicide triazolopyrimid-7-ylidenamine |
| US6747033B2 (en) | 2000-06-13 | 2004-06-08 | Basf Aktiengesellschaft | Fungicidal triazolopyrimid-7-ylideneamines |
| CA2420217A1 (en) * | 2000-08-25 | 2002-02-28 | Basf Aktiengesellschaft | Fungicidal formulation |
| DE60013188T2 (de) * | 2000-12-06 | 2004-12-30 | Basf Ag | Fungiizide 6-(trifluormethyl-phenyl)-triazolpyrimidine |
| DE10063115A1 (de) * | 2000-12-18 | 2002-06-27 | Bayer Ag | Triazolopyrimidine |
| ATE270292T1 (de) * | 2001-04-09 | 2004-07-15 | Basf Ag | Fungizide 5-alkylamino-6-phenyl-7-halogen- triazolopyrimidine |
| ATE274518T1 (de) | 2001-04-11 | 2004-09-15 | Basf Ag | 6-(2-chlor-6-fluor-phenyl)-triazolpyrimidine |
| ATE287405T1 (de) | 2001-04-11 | 2005-02-15 | Wyeth Corp | 5-halogen-6-phenyl-7-fluoroalkylamino- triazolopyrimidine als fungizide |
| DE10121101A1 (de) * | 2001-04-27 | 2002-10-31 | Bayer Ag | Triazolopyrimidine |
| DE10121162A1 (de) | 2001-04-30 | 2002-10-31 | Bayer Ag | Triazolopyrimidine |
| DE10124208A1 (de) * | 2001-05-18 | 2002-11-21 | Bayer Ag | Verwendung von Triazolopyrimidin-Derivaten als Mikrobizide |
| US7300908B2 (en) | 2001-07-05 | 2007-11-27 | Basf Aktiengesellschaft | Fungicidal triazolopyrimidines, method for the production thereof and use thereof in controlling noxious fungi and agents containing said compounds |
| HUP0401746A3 (en) * | 2001-07-18 | 2008-02-28 | Basf Ag | Substituted 6-(2-tolyl)-triazolopyrimidines as fungicides |
| KR20040015816A (ko) * | 2001-07-18 | 2004-02-19 | 바스프 악티엔게젤샤프트 | 살진균제로서 6-(2,6-디플루오로-페닐)-트리아졸로피리미딘 |
| JP2005504743A (ja) * | 2001-07-18 | 2005-02-17 | ビーエーエスエフ アクチェンゲゼルシャフト | 殺菌薬としての置換された６−（２−メトキシ−フェニル）−トリアゾロピリミジン |
| UA76486C2 (en) | 2001-07-26 | 2006-08-15 | Basf Ag | 7-amino triazolopyrimidines, a process of praparation, a fungicidal preparations based thereon and a method to control phytopathogenic fungi |
| US7211545B2 (en) | 2001-09-04 | 2007-05-01 | Sumitomo Chemical Company, Limited | Imidazo[1,2-a]pyrimidine and fungicidal compositions containing thereof |
| GB0126914D0 (en) * | 2001-11-08 | 2002-01-02 | Syngenta Ltd | Fungicides |
| WO2003080615A1 (de) | 2002-03-21 | 2003-10-02 | Basf Aktiengesellschaft | Fungizide triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel |
| DE10212886A1 (de) * | 2002-03-22 | 2003-10-02 | Bayer Cropscience Ag | Triazolopyrimidine |
| UA80304C2 (en) * | 2002-11-07 | 2007-09-10 | Basf Ag | Substituted 6-(2-halogenphenyl)triazolopyrimidines |
| JP2006514676A (ja) * | 2002-11-15 | 2006-05-11 | ビーエーエスエフ アクチェンゲゼルシャフト | ２−メルカプト置換トリアゾロピリミジン類、それらを製造するための方法、病原性菌類を防除するためのそれらの使用、及び、２−メルカプト置換トリアゾロピリミジン化合物を含んでいる薬剤 |
| PL377688A1 (pl) * | 2002-12-17 | 2006-02-06 | Basf Aktiengesellschaft | Grzybobójcze triazolopirymidyny, sposoby ich wytwarzania, ich zastosowanie do zwalczania szkodliwych grzybów i zawierające je środki |
| US20060211573A1 (en) * | 2003-03-31 | 2006-09-21 | Blasco Jordi T | 7-(Akenylamino)triazolopyrimidines, method for the production thereof and use thereof in controlling harmful fungi and substances containing said triazolopyrimidines |
| US20060211711A1 (en) * | 2003-04-02 | 2006-09-21 | Blasco Jordi T I | 7-(Alkinylamino)-triazolopyrimidines, methods for the production and use thereof to combat harmful fungi and agents containing said compounds |
| TW200504073A (en) * | 2003-04-17 | 2005-02-01 | Basf Ag | Bicyclic compounds and their use for controlling harmful fungi |
| UY28506A1 (es) * | 2003-09-12 | 2005-04-29 | Basf Ag | 6-halógeno-(1,2,4)triazolo(1,5-a)pirimidinas para combatir plagas animales. |
| 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 |
| MXPA06003206A (es) | 2003-09-24 | 2006-06-23 | Wyeth Corp | 6-[(sustituido)fenil]triazolopirimidinas como agentes anticancer. |
| JP4695595B2 (ja) | 2003-09-24 | 2011-06-08 | ワイス・ホールディングズ・コーポレイション | 抗癌剤としての６−アリール−７−ハロ−イミダゾ［１，２−ａ］ピリミジン類 |
| MY179926A (en) | 2003-12-08 | 2020-11-19 | Wyeth Corp | Process for the preparation of tubulin inhibitors |
| JP2007514689A (ja) * | 2003-12-18 | 2007-06-07 | ビーエーエスエフ アクチェンゲゼルシャフト | ６−（２−ハロフェニル）トリアゾロピリミジン、その製造方法、および植物病原性真菌類を防除するためのその使用、さらにはその物質を含有している農薬 |
| EP1720879A2 (de) * | 2004-02-25 | 2006-11-15 | Basf Aktiengesellschaft | Azolopyrimidin-verbindungen und ihre verwendung zur bekämpfung von schadpilzen |
| BRPI0510804A (pt) * | 2004-05-17 | 2007-11-06 | Basf Ag | compostos, uso de um composto, agente adequado para combater fungos nocivos, e, processo para combater fungos fitopatogênicos |
| CN1964629A (zh) * | 2004-06-09 | 2007-05-16 | 巴斯福股份公司 | 三唑并嘧啶化合物及其在防治有害真菌中的用途 |
| JP2008503512A (ja) * | 2004-06-22 | 2008-02-07 | ビーエーエスエフ アクチェンゲゼルシャフト | ６−（２−フルオロフェニル）−トリアゾロピリミジン、その生産方法、有害菌類を防除するためのその使用、およびそれを含有している薬剤 |
| EP1761543A1 (de) * | 2004-06-22 | 2007-03-14 | Basf Aktiengesellschaft | Verwendung von 6-(2-tolyl)-triazolopyrimidinen als fungizide, neue 6-(2-tolyl)-triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung |
| EA200700007A1 (ru) * | 2004-06-25 | 2007-08-31 | Басф Акциенгезельшафт | Триазолопиримидиновые соединения и их применение для борьбы с патогенными грибами |
| ATE383362T1 (de) * | 2004-07-08 | 2008-01-15 | Basf Ag | Substituierte 6-phenyl-7-amino-triazolopyrimidine,verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel |
| AU2005281882A1 (en) * | 2004-09-08 | 2006-03-16 | Basf Aktiengesellschaft | 6-phenyl-7-amino-triazolopyrimidines, methods for the production thereof, the use thereof for controlling pathogenic fungi, and agents containing the same |
| EP1853608B1 (de) * | 2005-02-16 | 2008-07-09 | Basf Se | 5-alkoxyalkyl-6-alkyl-7-amino-azolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel |
| AR059649A1 (es) * | 2006-02-28 | 2008-04-16 | Basf Ag | 6- fenil 7-amino - amino (1,2,4) -triazolo (1,5-a) pirimidinas y su su uso para el combate de hongos daninos |
| RU2325390C1 (ru) * | 2007-01-29 | 2008-05-27 | Государственное образовательное учреждение высшего профессионального образования "Южно-Российский государственный технический университет (Новочеркасский политехнический институт)" | СПОСОБ ПОЛУЧЕНИЯ 2-СУЛЬФОНИЛАМИНО-1,2,4,-ТРИАЗОЛО[1,5-a] ПИРИМИДИНОВ |
| EP1952691A3 (en) | 2007-01-31 | 2008-09-17 | Basf Se | Method for improving plant health by application of a triazolopyrimidine derivative |
| EP1952690A3 (en) | 2007-01-31 | 2009-04-22 | Basf Se | Pesticidal mixtures based on triazolopyrimidines and insecticides |
| RU2460298C1 (ru) * | 2011-05-03 | 2012-09-10 | Михаил Аркадьевич Ершов | Стимулятор для предпосевной обработки семян зерновых культур |
| RU2461197C1 (ru) * | 2011-05-03 | 2012-09-20 | Михаил Аркадьевич Ершов | Стимулятор для предпосевной обработки семян зерновых культур |
| RU2460297C1 (ru) * | 2011-05-04 | 2012-09-10 | Михаил Аркадьевич Ершов | Способ стимуляции всхожести семян |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1567021A (env) * | 1967-01-27 | 1969-05-16 | ||
| DE3130633A1 (de) | 1981-08-01 | 1983-02-17 | Basf Ag, 6700 Ludwigshafen | 7-amino-azolo(1,5-a)pyrimidine und diese enthaltende fungizide |
| HU208693B (en) * | 1991-02-22 | 1993-12-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing 1,2,4-triazolo (1,5-a) pyrimidinis derivatives and their carbicycli-tetrahydro-thiofurane-tetrahydrothiopyrane-, or tetrahydropyridine- condensated derivatives or medical preparatives containing them |
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