ZA200401516B - 7-amino triazolopyrimidines for controlling harmful fungi. - Google Patents

7-amino triazolopyrimidines for controlling harmful fungi. Download PDF

Info

Publication number: ZA200401516B
Authority: ZA; South Africa
Prior art keywords: formula; radicals; compounds; combination; nitrogen atoms
Prior art date: 2001-07-26

Application number

ZA200401516A

Other languages

English (en)

Inventor

Eberhard Ammermann

Markus Gewehr

Wassilios Grammenos

Thomas Grote

Andreas Gypser

Gisela Lorenz

Bernd Mueller

Joachim Rheinheimer

Ingo Rose

Hubert Sauter

Frank Schieweck

Peter Schaefer

Reinhard Stierl

Siegfried Strathmann

Jordi Tormo I Blasco

Original Assignee

Basf Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2001-07-26

Filing date

2004-02-25

Publication date

2005-03-10

2004-02-25 Application filed by Basf Ag filed Critical Basf Ag

2005-03-10 Publication of ZA200401516B publication Critical patent/ZA200401516B/en

Links

HRYKDUPGBWLLHO-UHFFFAOYSA-N 8-azaadenine Chemical class NC1=NC=NC2=NNN=C12 HRYKDUPGBWLLHO-UHFFFAOYSA-N 0.000 title claims description 21
241000233866 Fungi Species 0.000 title claims description 13
150000001875 compounds Chemical class 0.000 claims description 217
-1 nitro, hydroxyl Chemical group 0.000 claims description 179
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
125000004430 oxygen atom Chemical group O* 0.000 claims description 17
125000004093 cyano group Chemical group *C#N 0.000 claims description 16
229910052736 halogen Inorganic materials 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 14
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238000006243 chemical reaction Methods 0.000 claims description 12
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
239000011593 sulfur Substances 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
229910052783 alkali metal Inorganic materials 0.000 claims description 9
150000001340 alkali metals Chemical class 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 8
239000000543 intermediate Substances 0.000 claims description 8
230000002140 halogenating effect Effects 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
ODPJQZNJZWLTJH-UHFFFAOYSA-N 2,3-dihydrotriazolo[4,5-d]pyrimidin-5-one Chemical class O=C1N=CC2=NNNC2=N1 ODPJQZNJZWLTJH-UHFFFAOYSA-N 0.000 claims description 4
OEEYCNOOAHGFHL-UHFFFAOYSA-N 8-azahypoxanthine Chemical class O=C1N=CN=C2NNN=C12 OEEYCNOOAHGFHL-UHFFFAOYSA-N 0.000 claims description 4
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125000003545 alkoxy group Chemical group 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
125000004989 dicarbonyl group Chemical group 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
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238000004519 manufacturing process Methods 0.000 claims 2
208000014797 chronic intestinal pseudoobstruction Diseases 0.000 claims 1
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239000002689 soil Substances 0.000 claims 1
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125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 2
MEHWOCVPNCEIJO-UHFFFAOYSA-N 3-methyl-2,2-di(propan-2-yl)butan-1-amine Chemical compound CC(C)C(CN)(C(C)C)C(C)C MEHWOCVPNCEIJO-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
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ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
125000003302 alkenyloxy group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
150000004791 alkyl magnesium halides Chemical class 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
125000005133 alkynyloxy group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 1
125000005997 bromomethyl group Chemical group 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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 description 1
238000001212 derivatisation Methods 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 1
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
230000029087 digestion Effects 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
125000004438 haloalkoxy group Chemical group 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
150000004761 hexafluorosilicates Chemical class 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
150000002484 inorganic compounds Chemical class 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
229910052808 lithium carbonate Inorganic materials 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
229910001947 lithium oxide Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 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
231100000989 no adverse effect Toxicity 0.000 description 1
239000003921 oil Substances 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229930195734 saturated hydrocarbon Chemical group 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
229910001948 sodium oxide Inorganic materials 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
125000005537 sulfoxonium group Chemical group 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound 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
229910052720 vanadium Inorganic materials 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth 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)
Nitrogen Condensed Heterocyclic Rings (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)

ZA200401516A 2001-07-26 2004-02-25 7-amino triazolopyrimidines for controlling harmful fungi. ZA200401516B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE10136118		2001-07-26

Publications (1)

Publication Number	Publication Date
ZA200401516B true ZA200401516B (en)	2005-03-10

Family

ID=7692972

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200401516A ZA200401516B (en)	2001-07-26	2004-02-25	7-amino triazolopyrimidines for controlling harmful fungi.

Country Status (24)

Country	Link
US (1)	US7307172B2 (pl)
EP (1)	EP1414302B1 (pl)
JP (1)	JP4421893B2 (pl)
KR (1)	KR20040017347A (pl)
CN (1)	CN1318423C (pl)
AT (1)	ATE357142T1 (pl)
AU (1)	AU2002355178B2 (pl)
BR (1)	BR0211427A (pl)
CA (1)	CA2454542A1 (pl)
CO (1)	CO5550398A2 (pl)
DE (1)	DE50209786D1 (pl)
DK (1)	DK1414302T3 (pl)
EA (1)	EA006133B1 (pl)
ES (1)	ES2283626T3 (pl)
HU (1)	HUP0401488A2 (pl)
IL (1)	IL159607A0 (pl)
MX (1)	MXPA04000403A (pl)
NZ (1)	NZ531169A (pl)
PL (1)	PL368677A1 (pl)
PT (1)	PT1414302E (pl)
SI (1)	SI1414302T1 (pl)
UA (1)	UA76486C2 (pl)
WO (1)	WO2003009687A1 (pl)
ZA (1)	ZA200401516B (pl)

Families Citing this family (34)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU2003283348A1 (en) *	2002-11-07	2004-06-07	Basf Aktiengesellschaft	5-alkyl-7-aminotriazolopyrimidines, methods and intermediary products necessary for the production thereof, agents containing said compounds and the use thereof for fighting against harmful mushrooms
DE102004008807A1 (de)	2004-02-20	2005-09-08	Bayer Cropscience Ag	Pyrazolopyrimidine
EP1720879A2 (de) *	2004-02-25	2006-11-15	Basf Aktiengesellschaft	Azolopyrimidin-verbindungen und ihre verwendung zur bekämpfung von schadpilzen
EP1725560B1 (de) *	2004-03-10	2010-07-07	Basf Se	5,6-dialkyl-7-amino-triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel
KR20060130719A (ko) *	2004-03-10	2006-12-19	바스프 악티엔게젤샤프트	5,6-디히드로카르빌-7-아미노-트리아졸로피리미딘, 그의제조 방법, 그의 병원성 진균류 방제를 위한 용도 및 상기화합물을 포함하는 제제
DE502005009862D1 (de) *	2004-03-10	2010-08-19	Basf Se	5,6-dialkyl-7-aminotriazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel
DE102005007534A1 (de)	2005-02-17	2006-08-31	Bayer Cropscience Ag	Pyrazolopyrimidine
US20080139581A1 (en) *	2005-03-02	2008-06-12	Basf Aktiengesellschaft	2-Substituted 7-Aminoazolopyrimidines, Processes For Their Preparation And Their Use For Controlling Harmful Fungi, And Compositions Comprising These Compounds
US20080146839A1 (en) *	2005-03-18	2008-06-19	Basf Aktiengesellschaft	Method for Producing 5-Halo-2,4,6-Trifluoroisophthalic Acid
WO2007006724A1 (de) *	2005-07-13	2007-01-18	Basf Aktiengesellschaft	5-alkyl-7-amino-6-heteroaryl-1 , 2 , 4-triazolo (1 , 5-a) pyrimidin-vξrbindungen und ihre? verwendung zur bekämpfung von schadpilzen
AU2006274070C1 (en) *	2005-07-27	2012-03-29	Basf Se	Fungicidal mixtures based on azolopyrimidinylamines
WO2007113136A1 (de) *	2006-03-30	2007-10-11	Basf Aktiengesellschaft	Verwendung von substituierten riazolopyrimidinen zur bekämpfung von phyto pathogenen schadpilzen
WO2007116011A2 (de) *	2006-04-10	2007-10-18	Basf Se	Substituierte triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel
US20080027079A1 (en) *	2006-06-22	2008-01-31	Board Of Regents, University Of Texas System	Dihydroorotate dehydrogenase inhibitors with selective anti-malarial activity
WO2008034787A2 (en)	2006-09-18	2008-03-27	Basf Se	Pesticidal mixtures comprising an anthranilamide insecticide and a fungicide
US8791046B2 (en)	2006-11-10	2014-07-29	Basf Se	Crystalline modification of fipronil
JP5931322B2 (ja)	2006-11-10	2016-06-08	ビーエーエスエフソシエタス・ヨーロピアＢａｓｆＳｅ	フィプロニルの結晶変態
UA110598C2 (uk)	2006-11-10	2016-01-25	Басф Се	Спосіб одержання кристалічної модифікації фіпронілу
BRPI0718717A2 (pt)	2006-11-10	2013-11-26	Basf Se	Modificação cristalina ii de fipronil, fipronil sólido, processo para preparar a modificação cristalina ii, mistura pesticida ou parasiticida sinergística, composição pesticida ou parasiticida, uso da modificação cristalina ii, ou do fipronil sólido, ou da mistura, ou da composição, métodos para controlar pragas, para proteger uma planta da infestação e ataque por pragas, para proteger semente, e para tratar, controlar, prevenir ou proteger animais contra infestação ou infecção por parasitas, semente, uso da modificação cristalina ii, ou do fipronil sólido, ou da mistura, ou da composição, e, processo para a preparação de uma composição para trtar, controlar, prevenir ou proteger animais contra infestação ou infecção por parasitas
WO2008084082A1 (de) *	2007-01-11	2008-07-17	Basf Se	Verfahren zur herstellung arylsubstituierter anellierter pyrimidine
AU2008206921B2 (en)	2007-01-19	2012-11-01	Basf Se	Fungicidal mixtures of 1-methylpyrazole-4-ylcarboxylic acid anilides and azolopyrimidinylamines
EP2131658A2 (en) *	2007-01-30	2009-12-16	Basf Se	Method for improving plant health
JP5351047B2 (ja) *	2007-01-30	2013-11-27	ビーエーエスエフソシエタス・ヨーロピア	アゾロピリミジニルアミン誘導体及び殺虫剤を主成分とする殺虫性混合物
EP2679094A1 (en)	2007-02-06	2014-01-01	Basf Se	Pesticidal mixtures
NZ600929A (en)	2007-09-20	2014-02-28	Basf Se	Combinations comprising a fungicidal strain and an active compound
CA2772147C (en)	2009-09-16	2018-02-27	Basf Se	Method for reducing nitrous oxide emission from soils
US20130023412A1 (en)	2010-03-26	2013-01-24	Basf Se	Fungicidal Mixtures Based on Azolopyrimidinylamines
WO2011131602A2 (en)	2010-04-20	2011-10-27	Basf Se	Fungicidal mixtures based on azolopyrimmidinylamines
WO2011138345A2 (en)	2010-05-06	2011-11-10	Basf Se	Fungicidal mixtures based on gallic acid esters
AU2011347752A1 (en)	2010-12-20	2013-07-11	Basf Se	Pesticidal active mixtures comprising pyrazole compounds
US20140200136A1 (en)	2011-09-02	2014-07-17	Basf Se	Agricultural mixtures comprising arylquinazolinone compounds
US9474277B2 (en)	2012-06-20	2016-10-25	Basf Se	Pyrazole compound and pesticidal mixtures comprising a pyrazole compound
FR3034305B1 (fr)	2015-04-03	2021-10-15	Scaljet	Scalpel
JP7224548B2 (ja)	2020-06-01	2023-02-17	ユニマテック株式会社	含フッ素縮環ピリミジン化合物およびその製造方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3338292A1 (de)	1983-10-21	1985-05-02	Basf Ag, 6700 Ludwigshafen	7-amino-azolo(1,5-a)-pyrimidine und diese enthaltende fungizide
TW224044B (pl)	1991-12-30	1994-05-21	Shell Internat Res Schappej B V
US5387747A (en)	1992-02-24	1995-02-07	Laboratoires Upsa	Triazolopyrimidine derivatives which are angiotensin II receptor antagonists, their methods of preparation and pharmaceutical compositions in which they are present
FR2687676B1 (fr)	1992-02-24	1994-07-08	Union Pharma Scient Appl	Nouveaux derives de polyazaindenes antagonistes des recepteurs a l'angiotensine ii; leurs procedes de preparation, compositions pharmaceutiques les contenant.
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
RU2147584C1 (ru)	1995-10-27	2000-04-20	Американ Цианамид Компани	Способ получения дигалоидазолопиримидинов и способ получения дигидроксиазолопиримидинов
TW460476B (en)	1997-04-14	2001-10-21	American Cyanamid Co	Fungicidal trifluoromethylalkylamino-triazolopyrimidines

2002
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- 2002-07-16 UA UA2004021341A patent/UA76486C2/uk unknown
- 2002-07-16 EP EP02790165A patent/EP1414302B1/de not_active Expired - Lifetime
- 2002-07-16 SI SI200230527T patent/SI1414302T1/sl unknown
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- 2002-07-16 PT PT02790165T patent/PT1414302E/pt unknown
- 2002-07-16 DE DE50209786T patent/DE50209786D1/de not_active Expired - Lifetime
- 2002-07-16 PL PL02368677A patent/PL368677A1/pl not_active Application Discontinuation
- 2002-07-16 DK DK02790165T patent/DK1414302T3/da active
- 2002-07-16 WO PCT/EP2002/007893 patent/WO2003009687A1/de not_active Ceased
- 2002-07-16 EA EA200400111A patent/EA006133B1/ru not_active IP Right Cessation
- 2002-07-16 KR KR10-2004-7001010A patent/KR20040017347A/ko not_active Abandoned
- 2002-07-16 BR BR0211427-5A patent/BR0211427A/pt not_active Application Discontinuation
- 2002-07-16 AT AT02790165T patent/ATE357142T1/de not_active IP Right Cessation
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- 2002-07-16 CN CNB028147219A patent/CN1318423C/zh not_active Expired - Fee Related
- 2002-07-16 US US10/484,250 patent/US7307172B2/en not_active Expired - Fee Related
- 2002-07-16 JP JP2003515089A patent/JP4421893B2/ja not_active Expired - Fee Related
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2004
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Also Published As

Publication number	Publication date
JP2004535472A (ja)	2004-11-25
CN1318423C (zh)	2007-05-30
JP4421893B2 (ja)	2010-02-24
SI1414302T1 (sl)	2007-08-31
CO5550398A2 (es)	2005-08-31
DE50209786D1 (de)	2007-05-03
PL368677A1 (pl)	2005-04-04
EA200400111A1 (ru)	2004-06-24
IL159607A0 (en)	2004-06-01
DK1414302T3 (da)	2007-06-18
BR0211427A (pt)	2004-07-13
US20050261314A1 (en)	2005-11-24
KR20040017347A (ko)	2004-02-26
UA76486C2 (en)	2006-08-15
ES2283626T3 (es)	2007-11-01
WO2003009687A1 (de)	2003-02-06
ATE357142T1 (de)	2007-04-15
PT1414302E (pt)	2007-05-31
NZ531169A (en)	2005-09-30
US7307172B2 (en)	2007-12-11
MXPA04000403A (es)	2004-03-18
EP1414302B1 (de)	2007-03-21
CN1535113A (zh)	2004-10-06
EP1414302A1 (de)	2004-05-06
EA006133B1 (ru)	2005-10-27
CA2454542A1 (en)	2003-02-06
HUP0401488A2 (hu)	2004-12-28
AU2002355178B2 (en)	2007-08-02

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