CZ20033129A3 - Použití derivátů triazolopyrimidinu jako mikrobicidu při ochraně materiálů - Google Patents

Info

Publication number

CZ20033129A3

CZ20033129A3 CZ20033129A CZ20033129A CZ20033129A3 CZ 20033129 A3 CZ20033129 A3 CZ 20033129A3 CZ 20033129 A CZ20033129 A CZ 20033129A CZ 20033129 A CZ20033129 A CZ 20033129A CZ 20033129 A3 CZ20033129 A3 CZ 20033129A3

Authority

CZ

Czechia

Prior art keywords

atoms

group

phenyl

substituted

optionally

Prior art date

2001-05-18

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• 239000000463 material Substances 0.000 title claims abstract description 33
• 230000003641 microbiacidal effect Effects 0.000 title claims abstract description 13
• 229940124561 microbicide Drugs 0.000 title claims abstract description 7
• 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 title abstract description 11
• 150000001875 compounds Chemical class 0.000 claims abstract description 38
• 239000000203 mixture Substances 0.000 claims abstract description 22
• 239000002253 acid Substances 0.000 claims abstract description 18
• 150000003839 salts Chemical class 0.000 claims abstract description 17
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
• 229910052751 metal Inorganic materials 0.000 claims abstract description 13
• 239000002184 metal Substances 0.000 claims abstract description 13
• 244000005700 microbiome Species 0.000 claims abstract description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 5
• 239000003085 diluting agent Substances 0.000 claims abstract description 5
• 238000000034 method Methods 0.000 claims abstract description 5
• 239000002904 solvent Substances 0.000 claims abstract description 5
• 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 5
• 230000006378 damage Effects 0.000 claims abstract description 4
• 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 3
• 230000000845 anti-microbial effect Effects 0.000 claims abstract 3
• -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 138
• 125000004432 carbon atom Chemical group C* 0.000 claims description 28
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
• 239000000460 chlorine Substances 0.000 claims description 14
• 229910052736 halogen Inorganic materials 0.000 claims description 14
• 150000002367 halogens Chemical class 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
• 229910052801 chlorine Inorganic materials 0.000 claims description 12
• 229910052739 hydrogen Inorganic materials 0.000 claims description 12
• 239000001257 hydrogen Substances 0.000 claims description 12
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
• 241000233866 Fungi Species 0.000 claims description 9
• 239000002023 wood Substances 0.000 claims description 9
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
• 229910052794 bromium Inorganic materials 0.000 claims description 8
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• 239000011737 fluorine Substances 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
• 125000001188 haloalkyl group Chemical group 0.000 claims description 6
• 230000000844 anti-bacterial effect Effects 0.000 claims description 4
• 125000004429 atom Chemical group 0.000 claims description 4
• 239000003899 bactericide agent Substances 0.000 claims description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 239000000417 fungicide Substances 0.000 claims description 4
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
• 150000002431 hydrogen Chemical class 0.000 claims description 4
• 239000002917 insecticide Substances 0.000 claims description 4
• 229910052757 nitrogen Inorganic materials 0.000 claims description 4
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 3
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
• 230000000895 acaricidal effect Effects 0.000 claims description 3
• 239000000642 acaricide Substances 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
• 239000005645 nematicide Substances 0.000 claims description 3
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
• 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 3
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
• 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 2
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 2
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
• 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 2
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 2
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
• 125000002785 azepinyl group Chemical group 0.000 claims description 2
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
• 125000001246 bromo group Chemical group Br* 0.000 claims description 2
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 2
• 125000001153 fluoro group Chemical group F* 0.000 claims description 2
• 230000002538 fungal effect Effects 0.000 claims description 2
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
• 239000002855 microbicide agent Substances 0.000 claims description 2
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
• 125000005936 piperidyl group Chemical group 0.000 claims description 2
• 239000004033 plastic Substances 0.000 claims description 2
• 229920003023 plastic Polymers 0.000 claims description 2
• 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 claims description 2
• 238000000576 coating method Methods 0.000 claims 3
• 239000004557 technical material Substances 0.000 claims 3
• 239000013543 active substance Substances 0.000 claims 2
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 1
• 239000006057 Non-nutritive feed additive Substances 0.000 claims 1
• 230000001066 destructive effect Effects 0.000 claims 1
• 125000006456 halo alkyl cycloalkyl group Chemical group 0.000 claims 1
• 239000003755 preservative agent Substances 0.000 claims 1
• 125000001475 halogen functional group Chemical group 0.000 abstract 1
• 239000004480 active ingredient Substances 0.000 description 8
• 239000010949 copper Substances 0.000 description 8
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
• 150000007513 acids Chemical class 0.000 description 6
• 229910052802 copper Inorganic materials 0.000 description 6
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
• 239000000843 powder Substances 0.000 description 6
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
• LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 5
• BXKKQFGRMSOANI-UHFFFAOYSA-N 1-methoxy-3-[4-[(2-methoxy-2,4,4-trimethyl-3h-chromen-7-yl)oxy]phenyl]-1-methylurea Chemical compound C1=CC(NC(=O)N(C)OC)=CC=C1OC1=CC=C2C(C)(C)CC(C)(OC)OC2=C1 BXKKQFGRMSOANI-UHFFFAOYSA-N 0.000 description 4
• CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
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• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
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• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
• 229910052725 zinc Inorganic materials 0.000 description 4
• 239000011701 zinc Substances 0.000 description 4
• YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 3
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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