ZA200400914B - Fungicidal traizolopyrimidines, method for the production thereof and use thereof in controlling noxious fungi and agents containing said compounds. - Google Patents
Fungicidal traizolopyrimidines, method for the production thereof and use thereof in controlling noxious fungi and agents containing said compounds. Download PDFInfo
- Publication number
- ZA200400914B ZA200400914B ZA200400914A ZA200400914A ZA200400914B ZA 200400914 B ZA200400914 B ZA 200400914B ZA 200400914 A ZA200400914 A ZA 200400914A ZA 200400914 A ZA200400914 A ZA 200400914A ZA 200400914 B ZA200400914 B ZA 200400914B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- formula
- halogen
- alkenyl
- alkoxy
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 28
- 241000233866 Fungi Species 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 230000000855 fungicidal effect Effects 0.000 title claims description 3
- 230000001473 noxious effect Effects 0.000 title 1
- -1 cyano, hydroxy Chemical group 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical group 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000001651 cyanato group Chemical group [*]OC#N 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 238000006114 decarboxylation reaction Methods 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000005133 alkynyloxy 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Chemical group 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004670 alkyl amino thio carbonyl group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000004671 dialkylaminothiocarbonyl group Chemical group 0.000 claims description 2
- 125000004989 dicarbonyl group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 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 claims 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims 1
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims 1
- 125000005087 alkynylcarbonyl group Chemical group 0.000 claims 1
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 230000002538 fungal effect Effects 0.000 claims 1
- 125000000262 haloalkenyl group Chemical group 0.000 claims 1
- 150000002366 halogen compounds Chemical class 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000002689 soil Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- JSIAIROWMJGMQZ-UHFFFAOYSA-N 2h-triazol-4-amine Chemical compound NC1=CNN=N1 JSIAIROWMJGMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- GWFWKFGXZMRDNO-UHFFFAOYSA-N 5-chloro-2h-triazolo[4,5-d]pyrimidine Chemical class ClC1=NC=C2N=NNC2=N1 GWFWKFGXZMRDNO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 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
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 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
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 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
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000019253 formic acid Nutrition 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
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 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
- 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
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 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
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 238000000926 separation method Methods 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
- 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000008096 xylene 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10132059 | 2001-07-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200400914B true ZA200400914B (en) | 2005-02-04 |
Family
ID=7690356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200400914A ZA200400914B (en) | 2001-07-05 | 2004-02-04 | Fungicidal traizolopyrimidines, method for the production thereof and use thereof in controlling noxious fungi and agents containing said compounds. |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US7300908B2 (es) |
| EP (3) | EP1406903B1 (es) |
| JP (1) | JP2004533485A (es) |
| KR (1) | KR100619216B1 (es) |
| CN (1) | CN1284782C (es) |
| AR (1) | AR036128A1 (es) |
| AT (1) | ATE353901T1 (es) |
| BR (1) | BR0210858A (es) |
| CA (1) | CA2452625A1 (es) |
| DE (1) | DE50209496D1 (es) |
| EA (1) | EA007164B1 (es) |
| ES (1) | ES2281535T3 (es) |
| HU (1) | HUP0400385A3 (es) |
| IL (1) | IL159604A0 (es) |
| MX (1) | MXPA04000045A (es) |
| NZ (1) | NZ530822A (es) |
| PL (1) | PL367776A1 (es) |
| WO (1) | WO2003004465A2 (es) |
| ZA (1) | ZA200400914B (es) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006515845A (ja) * | 2002-12-17 | 2006-06-08 | ビーエーエスエフ アクチェンゲゼルシャフト | 殺真菌性トリアゾロピリミジン、それらの製造方法及び有害真菌を抑制するためのそれらの使用、並びにそれらを含む組成物 |
| KR20050119172A (ko) * | 2003-03-31 | 2005-12-20 | 바스프 악티엔게젤샤프트 | 7-알케닐아미노-트리아졸로피리미딘, 그의 제조 방법 및유해 진균류를 방제하기 위한 그의 용도와 상기트리아졸로피리미딘을 함유하는 물질 |
| EA200601108A1 (ru) * | 2003-12-18 | 2006-12-29 | Басф Акциенгезельшафт | 6-(2-галогенфенил)триазолопиримидины, способ их получения и их применение для борьбы с патогенными грибами, а также содержащие их средства |
| JP2008501755A (ja) * | 2004-06-09 | 2008-01-24 | ビーエーエスエフ アクチェンゲゼルシャフト | １，２，４−トリアゾロ［１，５ａ］ピリミジン類および植物病原性真菌を抑制するためのその使用 |
| DE102004031158A1 (de) | 2004-06-28 | 2006-01-19 | Basf Ag | Verwendung von Ethergruppen enthaltenden Polymeren als Lösungsvermittler |
| BRPI0516140A (pt) * | 2004-09-28 | 2008-08-26 | Basf Ag | compostos, uso dos mesmos, agente para combater fungos fitopatogênicos, e, processo para combater fungos fitopatogênicos |
| WO2006066799A1 (de) * | 2004-12-17 | 2006-06-29 | Basf Aktiengesellschaft | 7-amino-6-heteroaryl-1,2,4-triazolo[1,5-a]pyrimidine und ihre verwendung zur bekämpfung von schadpilzen |
| BRPI0606988A2 (pt) | 2005-02-21 | 2010-03-23 | Basf Ag | composiÇço, uso de pelo menos um polÍmetro hiper-ramificado contendo Átomos de nitrogÊnio, processo para a preparaÇço de uma composiÇço de substÂncia ativa ou eficaz aquosa, e, agentes cosmÉtico, farmacÊutico, e de proteÇço de planta |
| AR054777A1 (es) | 2005-06-20 | 2007-07-18 | Basf Ag | Modificaciones cristalinas de piraclostrobina |
| EP2514310A1 (de) | 2005-09-13 | 2012-10-24 | ISAGRO S.p.A. | Verfahren zum Schutz vor Phytopathogenen mit Kiralaxyl, entsprechende Verwendung und Mittel hierzu |
| 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 |
| KR100790109B1 (ko) | 2006-11-09 | 2008-01-02 | 삼성전자주식회사 | 푸쉬 로드 및 그를 구비하는 슬라이딩형 휴대용 단말기 |
| US20100056371A1 (en) * | 2007-01-08 | 2010-03-04 | Basf Se | Use of Azolopyrimidines for Controlling Phytopathogenic Harmful Fungi |
| CA2698293A1 (en) | 2007-09-13 | 2009-03-26 | Thomas Subkowski | Use of hydrophobin polypeptides as penetration intensifiers |
| US20110312497A1 (en) | 2009-02-10 | 2011-12-22 | Basf Se | Use of hydrophobin as a spreading agent |
| EP2531548A1 (de) | 2010-02-05 | 2012-12-12 | Basf Se | Verfahren zur solubilisierung von hydrophoben wirkstoffen in wässrigem medium |
| PL2688405T3 (pl) | 2011-03-23 | 2018-05-30 | Basf Se | Kompozycje zawierające polimerowe, jonowe związki zawierające grupy imidazoliowe |
| EP3050919A1 (de) | 2015-01-29 | 2016-08-03 | Basf Se | Lignocellulosehaltige materialen enthaltend mischungen mit salzen von n-substituierten carbamidsäuren |
| AU2022413634A1 (en) | 2021-12-17 | 2024-06-27 | Basf Se | Lactones for enhancing the activity of antimicrobial agents |
| WO2023111296A1 (en) | 2021-12-17 | 2023-06-22 | Basf Se | Composition comprising an antimicrobial agent and a carboxamide |
| EP4289273A1 (en) | 2022-06-07 | 2023-12-13 | Basf Se | Composition comprising an antimicrobial agent and a n-cyclohexyldiazeniumdioxy salt |
| EP4385328A1 (en) | 2022-12-15 | 2024-06-19 | Basf Se | Alpha-hydroxyketones for enhancing the activity of antimicrobial agents |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2388579A (en) * | 1944-02-29 | 1945-11-06 | Univ Minnesota | Process of making heterocyclic compounds |
| BE472445A (es) * | 1946-04-11 | |||
| FR2490586A1 (fr) | 1980-09-24 | 1982-03-26 | Aerospatiale | Profil de pale pour voilure tournante d'aeronef |
| DE3130633A1 (de) | 1981-08-01 | 1983-02-17 | Basf Ag, 6700 Ludwigshafen | 7-amino-azolo(1,5-a)pyrimidine und diese enthaltende fungizide |
| TW224044B (es) | 1991-12-30 | 1994-05-21 | Shell Internat Res Schappej B V | |
| WO1994014809A1 (de) * | 1992-12-23 | 1994-07-07 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Anellierte uracilderivate |
| 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 |
| US5817663A (en) | 1996-10-07 | 1998-10-06 | American Cyanamid Company | Pentafluorophenylazolopyrimidines |
| TW460476B (en) | 1997-04-14 | 2001-10-21 | American Cyanamid Co | Fungicidal trifluoromethylalkylamino-triazolopyrimidines |
| US6057456A (en) * | 1997-10-16 | 2000-05-02 | Yale University | Transition metal-catalyzed process for preparing alpha-arylated carbonyl-containing compounds |
| WO1999033796A1 (fr) * | 1997-12-26 | 1999-07-08 | Nissin Food Products Co., Ltd. | Derives de 5-arylpyrrole |
| ES2212527T3 (es) * | 1998-02-11 | 2004-07-16 | Basf Aktiengesellschaft | 7-alquil-triazolopirimidinas fungicidas. |
-
2002
- 2002-07-03 KR KR1020047000089A patent/KR100619216B1/ko not_active IP Right Cessation
- 2002-07-03 DE DE50209496T patent/DE50209496D1/de not_active Expired - Fee Related
- 2002-07-03 US US10/482,216 patent/US7300908B2/en not_active Expired - Fee Related
- 2002-07-03 CN CNB028158946A patent/CN1284782C/zh not_active Expired - Fee Related
- 2002-07-03 CA CA002452625A patent/CA2452625A1/en not_active Abandoned
- 2002-07-03 HU HU0400385A patent/HUP0400385A3/hu unknown
- 2002-07-03 JP JP2003510633A patent/JP2004533485A/ja not_active Withdrawn
- 2002-07-03 EP EP02758297A patent/EP1406903B1/de not_active Expired - Lifetime
- 2002-07-03 NZ NZ530822A patent/NZ530822A/en unknown
- 2002-07-03 PL PL02367776A patent/PL367776A1/xx not_active Application Discontinuation
- 2002-07-03 EP EP05018654A patent/EP1616870A1/de not_active Withdrawn
- 2002-07-03 EA EA200400107A patent/EA007164B1/ru not_active IP Right Cessation
- 2002-07-03 BR BR0210858-5A patent/BR0210858A/pt not_active IP Right Cessation
- 2002-07-03 EP EP05018655A patent/EP1634863A1/de not_active Withdrawn
- 2002-07-03 IL IL15960402A patent/IL159604A0/xx unknown
- 2002-07-03 AT AT02758297T patent/ATE353901T1/de not_active IP Right Cessation
- 2002-07-03 WO PCT/EP2002/007340 patent/WO2003004465A2/de active IP Right Grant
- 2002-07-03 ES ES02758297T patent/ES2281535T3/es not_active Expired - Lifetime
- 2002-07-03 MX MXPA04000045A patent/MXPA04000045A/es not_active Application Discontinuation
- 2002-07-04 AR ARP020102513A patent/AR036128A1/es unknown
-
2004
- 2004-02-04 ZA ZA200400914A patent/ZA200400914B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20050090665A1 (en) | 2005-04-28 |
| WO2003004465A3 (de) | 2003-05-08 |
| EP1406903B1 (de) | 2007-02-14 |
| BR0210858A (pt) | 2004-06-29 |
| JP2004533485A (ja) | 2004-11-04 |
| EA200400107A1 (ru) | 2004-06-24 |
| AR036128A1 (es) | 2004-08-11 |
| CN1284782C (zh) | 2006-11-15 |
| ATE353901T1 (de) | 2007-03-15 |
| EP1634863A1 (de) | 2006-03-15 |
| CA2452625A1 (en) | 2003-01-16 |
| EP1406903A2 (de) | 2004-04-14 |
| MXPA04000045A (es) | 2004-05-21 |
| US7300908B2 (en) | 2007-11-27 |
| DE50209496D1 (de) | 2007-03-29 |
| HUP0400385A3 (en) | 2005-11-28 |
| PL367776A1 (en) | 2005-03-07 |
| CN1541218A (zh) | 2004-10-27 |
| EP1616870A1 (de) | 2006-01-18 |
| IL159604A0 (en) | 2004-06-01 |
| NZ530822A (en) | 2004-08-27 |
| KR100619216B1 (ko) | 2006-09-08 |
| KR20040010835A (ko) | 2004-01-31 |
| ES2281535T3 (es) | 2007-10-01 |
| WO2003004465A2 (de) | 2003-01-16 |
| EA007164B1 (ru) | 2006-08-25 |
| HUP0400385A2 (hu) | 2004-12-28 |
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