ZA200605805B - 6-(2-Chloro-4-alkoxy-phenyl)-triazolopyrimidine, method for the production thereof and its utilization for controlling fungi and the agents contained therein - Google Patents

Info

Publication number

ZA200605805B

ZA200605805B ZA200605805A ZA200605805A ZA200605805B ZA 200605805 B ZA200605805 B ZA 200605805B ZA 200605805 A ZA200605805 A ZA 200605805A ZA 200605805 A ZA200605805 A ZA 200605805A ZA 200605805 B ZA200605805 B ZA 200605805B

Authority

ZA

South Africa

Prior art keywords

formula

compounds

alkyl

compound

hydrogen

Prior art date

2003-12-17

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• 241000233866 Fungi Species 0.000 title claims description 15
• 238000000034 method Methods 0.000 title claims description 13
• 238000004519 manufacturing process Methods 0.000 title claims description 5
• 150000001875 compounds Chemical class 0.000 claims description 347
• -1 nitro, hydroxyl Chemical group 0.000 claims description 141
• 239000000460 chlorine Substances 0.000 claims description 102
• 229910052801 chlorine Inorganic materials 0.000 claims description 92
• 229910052739 hydrogen Inorganic materials 0.000 claims description 81
• 239000001257 hydrogen Substances 0.000 claims description 81
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 71
• 150000002431 hydrogen Chemical class 0.000 claims description 68
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 55
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 41
• 229910052736 halogen Inorganic materials 0.000 claims description 26
• 150000002367 halogens Chemical class 0.000 claims description 26
• 238000006243 chemical reaction Methods 0.000 claims description 21
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 21
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 21
• 125000000217 alkyl group Chemical group 0.000 claims description 18
• 239000000203 mixture Substances 0.000 claims description 18
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
• 229910052760 oxygen Inorganic materials 0.000 claims description 13
• 125000005842 heteroatom Chemical group 0.000 claims description 12
• 125000001424 substituent group Chemical group 0.000 claims description 12
• 229910052717 sulfur Inorganic materials 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• 125000001188 haloalkyl group Chemical group 0.000 claims description 10
• 229910052783 alkali metal Inorganic materials 0.000 claims description 9
• 125000001072 heteroaryl group Chemical group 0.000 claims description 9
• 125000000623 heterocyclic group Chemical group 0.000 claims description 9
• 239000000463 material Substances 0.000 claims description 9
• 150000001340 alkali metals Chemical class 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 8
• 239000003795 chemical substances by application Substances 0.000 claims description 8
• 150000001412 amines Chemical class 0.000 claims description 7
• 229920006395 saturated elastomer Polymers 0.000 claims description 7
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
• 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
• 229910052794 bromium Inorganic materials 0.000 claims description 6
• 229910052799 carbon Inorganic materials 0.000 claims description 6
• 150000003254 radicals Chemical class 0.000 claims description 6
• 239000007787 solid Substances 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 5
• 125000004122 cyclic group Chemical group 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 239000000543 intermediate Substances 0.000 claims description 5
• 125000001624 naphthyl group Chemical group 0.000 claims description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
• 230000008569 process Effects 0.000 claims description 5
• 125000003118 aryl group Chemical group 0.000 claims description 4
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• 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
• 150000002690 malonic acid derivatives Chemical class 0.000 claims description 4
• 150000002825 nitriles Chemical class 0.000 claims description 4
• 230000003032 phytopathogenic effect Effects 0.000 claims description 4
• JSIAIROWMJGMQZ-UHFFFAOYSA-N 2h-triazol-4-amine Chemical compound NC1=CNN=N1 JSIAIROWMJGMQZ-UHFFFAOYSA-N 0.000 claims description 3
• 125000001931 aliphatic group Chemical group 0.000 claims description 3
• 125000003545 alkoxy group Chemical group 0.000 claims description 3
• 238000006114 decarboxylation reaction Methods 0.000 claims description 3
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• KVGVQTOQSNJTJI-UHFFFAOYSA-N 8-azaxanthine Chemical class O=C1NC(=O)NC2=C1NN=N2 KVGVQTOQSNJTJI-UHFFFAOYSA-N 0.000 claims description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
• 125000002723 alicyclic group Chemical group 0.000 claims description 2
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
• 125000003282 alkyl amino group Chemical group 0.000 claims description 2
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• 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
• 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 2
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• 125000004104 aryloxy group Chemical group 0.000 claims description 2
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• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 2
• 125000000468 ketone group Chemical group 0.000 claims description 2
• WWYDYZMNFQIYPT-UHFFFAOYSA-N ru78191 Chemical class OC(=O)C(C(O)=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-N 0.000 claims description 2
• 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 2
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• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
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• 239000000047 product Substances 0.000 description 10
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• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
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• 239000002270 dispersing agent Substances 0.000 description 8
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