AU2006274073A1 - 6-phenyl-pyrazolopyrimidine-7-ylamine fungicides - Google Patents

Info

Publication number

AU2006274073A1

AU2006274073A1 AU2006274073A AU2006274073A AU2006274073A1 AU 2006274073 A1 AU2006274073 A1 AU 2006274073A1 AU 2006274073 A AU2006274073 A AU 2006274073A AU 2006274073 A AU2006274073 A AU 2006274073A AU 2006274073 A1 AU2006274073 A1 AU 2006274073A1

Authority

AU

Australia

Prior art keywords

formula

alkyl

compounds

methyl

compound

Prior art date

2005-07-27

Legal status (The legal status 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 status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• Discuss

• KKEOHSAYYNDJJC-UHFFFAOYSA-N 6-phenylpyrazolo[4,3-d]pyrimidin-7-amine Chemical compound C1=NC2=CN=NC2=C(N)N1C1=CC=CC=C1 KKEOHSAYYNDJJC-UHFFFAOYSA-N 0.000 title claims abstract description 5
• 239000000417 fungicide Substances 0.000 title description 12
• 150000001875 compounds Chemical class 0.000 claims abstract description 122
• 241000233866 Fungi Species 0.000 claims abstract description 14
• 238000000034 method Methods 0.000 claims abstract description 9
• 230000003032 phytopathogenic effect Effects 0.000 claims abstract description 4
• -1 Cl-C 8 -alkoxy Chemical group 0.000 claims description 124
• 239000000203 mixture Substances 0.000 claims description 34
• 229910052736 halogen Inorganic materials 0.000 claims description 17
• 150000002367 halogens Chemical class 0.000 claims description 17
• 229910052739 hydrogen Inorganic materials 0.000 claims description 15
• 239000001257 hydrogen Substances 0.000 claims description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• 239000000463 material Substances 0.000 claims description 10
• 239000000460 chlorine Substances 0.000 claims description 8
• 125000001424 substituent group Chemical group 0.000 claims description 7
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 229920006395 saturated elastomer Polymers 0.000 claims description 6
• JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 claims description 5
• 150000002431 hydrogen Chemical class 0.000 claims description 5
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
• 239000007787 solid Substances 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• 229910052757 nitrogen Inorganic materials 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
• 229910021529 ammonia Inorganic materials 0.000 claims description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
• 229910052794 bromium Inorganic materials 0.000 claims description 3
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
• 125000004122 cyclic group Chemical group 0.000 claims description 3
• 230000000855 fungicidal effect Effects 0.000 claims description 3
• 239000002689 soil Substances 0.000 claims description 3
• JFZSDNLQDTYVEE-UHFFFAOYSA-N 1,4-dihydropyrazolo[4,3-d]pyrimidin-7-one Chemical class O=C1N=CNC2=C1NN=C2 JFZSDNLQDTYVEE-UHFFFAOYSA-N 0.000 claims description 2
• 150000001264 acyl cyanides Chemical class 0.000 claims description 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
• 230000002538 fungal effect Effects 0.000 claims description 2
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 4
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
• 238000004519 manufacturing process Methods 0.000 claims 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
• 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 1
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
• 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
• 239000007788 liquid Substances 0.000 claims 1
• 230000003071 parasitic effect Effects 0.000 abstract 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
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• 235000005822 corn Nutrition 0.000 description 14
• 235000009566 rice Nutrition 0.000 description 14
• 239000000839 emulsion Substances 0.000 description 13
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
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• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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• 235000010469 Glycine max Nutrition 0.000 description 6
• 244000068988 Glycine max Species 0.000 description 6
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
• 239000002253 acid Substances 0.000 description 6
• 150000001340 alkali metals Chemical class 0.000 description 6
• 125000000217 alkyl group Chemical group 0.000 description 6
• 239000000969 carrier Substances 0.000 description 6
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
• 125000003396 thiol group Chemical class [H]S* 0.000 description 6
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• 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 5
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• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
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• 240000006365 Vitis vinifera Species 0.000 description 5
• 150000007513 acids Chemical class 0.000 description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
• 239000006072 paste Substances 0.000 description 5
• 238000003786 synthesis reaction Methods 0.000 description 5
• PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
• MPDXYVOXVJOKIN-UHFFFAOYSA-N 1h-pyrazolo[4,3-d]pyrimidin-7-amine Chemical class NC1=NC=NC2=C1NN=C2 MPDXYVOXVJOKIN-UHFFFAOYSA-N 0.000 description 4
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
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• 240000003768 Solanum lycopersicum Species 0.000 description 4
• 235000002595 Solanum tuberosum Nutrition 0.000 description 4
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• 150000001298 alcohols Chemical class 0.000 description 4
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
• 239000011230 binding agent Substances 0.000 description 4
• 230000015572 biosynthetic process Effects 0.000 description 4
• 125000004432 carbon atom Chemical group C* 0.000 description 4
• 235000014113 dietary fatty acids Nutrition 0.000 description 4
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
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• 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 4
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
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• 125000004430 oxygen atom Chemical group O* 0.000 description 4
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
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• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
• 240000008067 Cucumis sativus Species 0.000 description 3
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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• PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 description 2
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