AU2004261373B8 - 2-substituted pyrimidines - Google Patents

Info

Publication number

AU2004261373B8

AU2004261373B8 AU2004261373A AU2004261373A AU2004261373B8 AU 2004261373 B8 AU2004261373 B8 AU 2004261373B8 AU 2004261373 A AU2004261373 A AU 2004261373A AU 2004261373 A AU2004261373 A AU 2004261373A AU 2004261373 B8 AU2004261373 B8 AU 2004261373B8

Authority

AU

Australia

Prior art keywords

compounds

alkyl

formulae

row

case

Prior art date

2003-07-24

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.)

Ceased

Links

• Espacenet
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• -1 2-substituted pyrimidines Chemical class 0.000 title claims description 186
• 150000001875 compounds Chemical class 0.000 claims description 517
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 76
• 229910052739 hydrogen Inorganic materials 0.000 claims description 69
• 239000001257 hydrogen Substances 0.000 claims description 67
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 66
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 58
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
• 150000002431 hydrogen Chemical class 0.000 claims description 27
• 125000001424 substituent group Chemical group 0.000 claims description 24
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• 150000002367 halogens Chemical class 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• 239000000460 chlorine Substances 0.000 claims description 14
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
• 241000233866 Fungi Species 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 12
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
• 239000011737 fluorine Substances 0.000 claims description 11
• 229910052731 fluorine Inorganic materials 0.000 claims description 11
• 238000000034 method Methods 0.000 claims description 11
• 150000002825 nitriles Chemical class 0.000 claims description 11
• 125000003342 alkenyl group Chemical group 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 10
• 125000001931 aliphatic group Chemical group 0.000 claims description 9
• 239000000463 material Substances 0.000 claims description 9
• 229920006395 saturated elastomer Polymers 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 7
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
• 125000000217 alkyl group Chemical group 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 150000001408 amides Chemical class 0.000 claims description 7
• 150000002148 esters Chemical class 0.000 claims description 7
• 150000001298 alcohols Chemical class 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
• 125000001651 cyanato group Chemical group [*]OC#N 0.000 claims description 6
• 239000007787 solid Substances 0.000 claims description 6
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 5
• 125000004429 atom Chemical group 0.000 claims description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
• 229910052740 iodine Inorganic materials 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 230000003032 phytopathogenic effect Effects 0.000 claims description 4
• 239000002689 soil Substances 0.000 claims description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
• 230000002538 fungal effect Effects 0.000 claims description 3
• 150000004820 halides Chemical class 0.000 claims description 3
• 230000007062 hydrolysis Effects 0.000 claims description 3
• 238000006460 hydrolysis reaction Methods 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 239000000575 pesticide Substances 0.000 claims description 3
• 230000008569 process Effects 0.000 claims description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
• 125000002723 alicyclic group Chemical group 0.000 claims description 2
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
• 125000003118 aryl group Chemical group 0.000 claims description 2
• 229910052799 carbon Inorganic materials 0.000 claims description 2
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
• 239000003795 chemical substances by application Substances 0.000 claims description 2
• 125000000623 heterocyclic group Chemical group 0.000 claims description 2
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
• 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 2
• 125000004962 sulfoxyl group Chemical group 0.000 claims description 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 7
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 7
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 4
• XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 2
• 239000007788 liquid Substances 0.000 claims 2
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims 1
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
• 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims 1
• SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
• 150000002463 imidates Chemical class 0.000 claims 1
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
• 150000002826 nitrites Chemical class 0.000 claims 1
• 229910052698 phosphorus Inorganic materials 0.000 claims 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 57
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
• 239000000203 mixture Substances 0.000 description 20
• 241000196324 Embryophyta Species 0.000 description 18
• IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 15
• 238000002360 preparation method Methods 0.000 description 14
• PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 13
• 239000006185 dispersion Substances 0.000 description 10
• 239000000417 fungicide Substances 0.000 description 10
• 239000003921 oil Substances 0.000 description 10
• 239000000047 product Substances 0.000 description 10
• 239000000243 solution Substances 0.000 description 10
• 238000010790 dilution Methods 0.000 description 9
• 239000012895 dilution Substances 0.000 description 9
• 125000001153 fluoro group Chemical group F* 0.000 description 9
• 239000008187 granular material Substances 0.000 description 9
• 150000003230 pyrimidines Chemical class 0.000 description 9
• 150000003254 radicals Chemical class 0.000 description 9
• 238000005160 1H NMR spectroscopy Methods 0.000 description 8
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
• 239000002270 dispersing agent Substances 0.000 description 8
• 239000000839 emulsion Substances 0.000 description 8
• 239000000843 powder Substances 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• 230000015572 biosynthetic process Effects 0.000 description 7
• 125000004432 carbon atom Chemical group C* 0.000 description 7
• 230000000694 effects Effects 0.000 description 7
• 239000003995 emulsifying agent Substances 0.000 description 7
• 239000011541 reaction mixture Substances 0.000 description 7
• 238000003786 synthesis reaction Methods 0.000 description 7
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• 239000002585 base Substances 0.000 description 6
• 239000000969 carrier Substances 0.000 description 6
• 235000013339 cereals Nutrition 0.000 description 6
• 238000006243 chemical reaction Methods 0.000 description 6
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
• 238000009472 formulation Methods 0.000 description 6
• 230000000855 fungicidal effect Effects 0.000 description 6
• 208000015181 infectious disease Diseases 0.000 description 6
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
• 239000002253 acid Substances 0.000 description 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
• 239000006072 paste Substances 0.000 description 5
• 239000002904 solvent Substances 0.000 description 5
• 239000008096 xylene Substances 0.000 description 5
• UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 description 4
• 239000004215 Carbon black (E152) Substances 0.000 description 4
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
• 235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
• 240000007594 Oryza sativa Species 0.000 description 4
• 235000007164 Oryza sativa Nutrition 0.000 description 4
• 240000003768 Solanum lycopersicum Species 0.000 description 4
• 229910052783 alkali metal Inorganic materials 0.000 description 4
• 235000014113 dietary fatty acids Nutrition 0.000 description 4
• 239000000194 fatty acid Substances 0.000 description 4
• 229930195729 fatty acid Natural products 0.000 description 4
• 229930195733 hydrocarbon Natural products 0.000 description 4
• 235000012054 meals Nutrition 0.000 description 4
• 229920000151 polyglycol Polymers 0.000 description 4
• 239000010695 polyglycol Substances 0.000 description 4
• 235000009566 rice Nutrition 0.000 description 4
• CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 4
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
• 235000013311 vegetables Nutrition 0.000 description 4
• 239000000080 wetting agent Substances 0.000 description 4
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
• 241000123650 Botrytis cinerea Species 0.000 description 3
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
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• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
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• 125000000753 cycloalkyl group Chemical group 0.000 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 description 3
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• 150000004665 fatty acids Chemical class 0.000 description 3
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