WO1986001207A1 - Pyridopyrimidine derivatives and process for their preparation - Google Patents
Pyridopyrimidine derivatives and process for their preparation Download PDFInfo
- Publication number
- WO1986001207A1 WO1986001207A1 PCT/JP1985/000441 JP8500441W WO8601207A1 WO 1986001207 A1 WO1986001207 A1 WO 1986001207A1 JP 8500441 W JP8500441 W JP 8500441W WO 8601207 A1 WO8601207 A1 WO 8601207A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- lower alkyl
- alkyl group
- hydrogen
- substituted
- Prior art date
Links
- 150000008518 pyridopyrimidines Chemical class 0.000 title claims description 11
- 238000000034 method Methods 0.000 title abstract description 12
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 65
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000002252 acyl group Chemical group 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 7
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 101
- 239000001257 hydrogen Substances 0.000 claims description 29
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000004575 stone Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- FUXJMHXHGDAHPD-UHFFFAOYSA-N pyrimidine-2-carboxamide Chemical class NC(=O)C1=NC=CC=N1 FUXJMHXHGDAHPD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical class O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 claims 1
- 230000006315 carbonylation Effects 0.000 claims 1
- 238000005810 carbonylation reaction Methods 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 230000001747 exhibiting effect Effects 0.000 claims 1
- -1 tetrahydropyranoxy group Chemical group 0.000 abstract description 32
- 239000004009 herbicide Substances 0.000 abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 238000000862 absorption spectrum Methods 0.000 description 24
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 23
- 238000002844 melting Methods 0.000 description 22
- 230000008018 melting Effects 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 230000002363 herbicidal effect Effects 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 150000001793 charged compounds Chemical class 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000001819 mass spectrum Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 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 5
- BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
- 238000009333 weeding Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 235000003332 Ilex aquifolium Nutrition 0.000 description 4
- 241000209027 Ilex aquifolium Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- CSBPQHGADOHBPJ-UHFFFAOYSA-N 6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=NC=C2C(=O)NC=CC2=N1 CSBPQHGADOHBPJ-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 210000003323 beak Anatomy 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004517 catalytic hydrocracking Methods 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical group C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- 125000005810 2,5-xylyl group Chemical group [H]C1=C([H])C(=C(*)C([H])=C1C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000254158 Lampyridae Species 0.000 description 1
- 241000237503 Pectinidae Species 0.000 description 1
- 241001387976 Pera Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- MNZMECMQTYGSOI-UHFFFAOYSA-N acetic acid;hydron;bromide Chemical compound Br.CC(O)=O MNZMECMQTYGSOI-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229940000489 arsenate Drugs 0.000 description 1
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- PIZLBWGMERQCOC-UHFFFAOYSA-N dibenzyl carbonate Chemical compound C=1C=CC=CC=1COC(=O)OCC1=CC=CC=C1 PIZLBWGMERQCOC-UHFFFAOYSA-N 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- DDNRNCSGIYDEMC-UHFFFAOYSA-N ethanol;formic acid Chemical compound CCO.OC=O DDNRNCSGIYDEMC-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 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
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- PLZDHJUUEGCXJH-UHFFFAOYSA-N pyrido[4,3-d]pyrimidine Chemical compound C1=NC=C2C=NC=CC2=N1 PLZDHJUUEGCXJH-UHFFFAOYSA-N 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000020637 scallop Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Definitions
- the present invention relates to a novel pyridopyrimidine derivative useful as a herbicide and a method for producing the same.
- the present invention is based on (1)-general formula [I] ⁇ li 3
- R 7 represents hydrogen, a lower alkyl group, an aralkyl group, a lower alkoxycarbonyl group, an aralkyloxycarbonyl group or an acyl group.
- J, R 2 is hydrogen or a lower alkyl group]
- R 3 is hydrogen, a lower alkyl group, an aralkyl group, an aryl group, a hydroxyl-substituted lower alkyl group, a lower alkoxy-substituted lower alkyl group
- Lanoxy group-substituted lower alkyl groups j and? 4 are hydrogen, lower alkyl groups or aralkyl groups. The same applies hereinafter.
- a method for producing the novel pyridopyrimidine derivative includes:
- R represents an aralkyl group xylcarbonyl or an acyl group among R 7 .
- R represents an aralkyl group xylcarbonyl or an acyl group among R 7 .
- R represents an aralkyl group xylcarbonyl or an acyl group among R 7 .
- R represents an aralkyl group xylcarbonyl or an acyl group among R 7 .
- R 8 represents a halogen, an alkoxy group and by the group et chosen Ru group of the nitro group] 9 unsubstituted or by good phenyl group optionally j9 substituted methyl group or hydrogen. The same applies hereinafter. ).
- Limidine derivative and general formula [w]
- the substance of the present invention is represented by the general formula [I].
- the lower alkyl group of the “phenyl group optionally substituted with a lower alkyl group” for R ! a methyl group, an ethyl group, a propyl group, and isoprohi.
- A a n-butyl group, an isobutyl group, a sec-butyl group, a ⁇ -butyl group, etc., among which a methyl group and an ethyl group are preferred, and the number of substitution with a lower alkyl group is usually 1 or 3].
- the number of substitutions is one.
- the phenyl group which may be substituted is preferably? Examples thereof include a 5-tolyl group and a V-ethylphenyl group.
- R is a group represented by the formula ( ⁇ )
- R 5 and R 6 are the same as those described above as the lower alkyl group, and the phenyl-substituted methyl group is a pendyl group, a diphenylmethyl group, or the like.
- the R 5 and 'R e are bonded to ⁇ alkylene group having 4 3 ⁇ 4 stone ⁇ carbon, particularly preferably one carbon teaching is 5.
- R 7 where R! Is a group represented by one ⁇ [[pi!],
- the lower alkyl group can be exemplified those listed before, preferably a methyl group, E Ji group,
- the aralkyl group include a benzyl group, a diphenylmethyl group, and a triphenylmethyl group. Of these, a benzyl group is preferable, and the aralkyl group is a benzyl group.
- Examples include diphenylenetinole, quinolone, and di-phenylene, and ⁇ -chlorophenylmethyloxycarbonyl, among which benzyloxycarbonyl is preferred.
- the lower alkoxycarbonyl is preferably Ethoxycarbonyl group, ethoxycarbonyl Examples thereof include a nore group, a propoxycarbinole group, an isopropoxycarbonyl group, and a ptoxylcarbonyl group, and among them, the former two groups are preferable.
- examples of the acyl group of R 7 include a formyl group, an acetyl group, an aromatic acyl such as a pionyl group, an aromatic acyl such as benzoyl and toluoyl, and among them, formyl and penzyl are preferred.
- examples of the lower alkyl group represented by? 2 and? 3 include those listed above.
- examples of the aralkyl group represented by R3 include those represented by R7, and the aryl group represented by phenyl group and 0.
- a phenyl group is preferable.
- methoxethyl is preferable.
- 2-tetrahydryl is preferred.
- the substance of the present invention is represented by the general formula [IV] (however, specific examples of R i or 4 in the formula are the same as those described in the description of the present substance. The same applies to other compounds hereinafter).
- a limidinidine carboxylic acid amide derivative By reacting a limidinidine carboxylic acid amide derivative with a formylating agent in the presence of a base.
- the compound represented by the general formula [W] can be obtained by the method described in the present applicant's application and the application filed on the same date and entitled “New limidine derivative and its production method” or a method based on the method, and further described below. Reference example: Which method is used?
- Examples of the formylating agent include N, N'-dimethylformamide, N, N'-getylformamide, methyl orthoformate, ethyl ethyl formate, methyl formate, and ethyl formate.
- N, N'-dimethylformamide and methyl formate are preferred.
- Examples of the base used in the reaction include NaII, NaNH 2 , LiH ⁇ LiNH 2 , LiN iso-pr) 2 , t-BOK ⁇ MeONa3 ⁇ 4, among which ⁇ ⁇ and t-BuOK Ka is preferred.
- the above-described formylating agent is also used as a solvent. Therefore, it is not necessary to use another solvent, but it may be used.
- other solvents such as hexane, benzene, toluene, and xylene may be used, such as hydrocarbon solvents, athenole, tetrahydrofuran, dithioxane, and dimethinoresnorreoxide. it can.
- N is usually used in a molar amount of 1 to 20 times, preferably 1 to 10 times the molar amount of the compound of the formula [N], and the base is usually used in a molar amount of 1 to 3 times.
- the reaction is usually carried out at a temperature of 20 to 25 (3 ° C, preferably 8 to 150 ° C) for 0.5 to 10 hours, depending on other conditions.
- Purification and isolation of the target compound can be carried out by a conventional method as described in Examples below.
- a compound represented by the general formula [I- ⁇ ] according to the present invention Lidohi.
- the lymidine derivative can be produced by hydrocracking the bilimidine derivative represented by the general formula [I-II] according to the present invention.
- the aralkyl groups for Ri include those listed for R 7 . This method can also be applied to the case of penzinolexyl carboxy, among the aranolequinoleoxycanoleboninole groups of R 7 . 1 ⁇
- ⁇ ⁇ -carbon Raney—Ni, pd0, etc. can be used as a hydrocracking catalyst.
- the amount of the catalyst used is 0.01 to 1 times (molar ratio) the compound [I--:].
- the reaction solvent is usually methanol, ethanol, or iso.
- -Acetic acid Using a mixed solvent and dioxane, usually under normal pressure or 10 atm, preferably under normal pressure or 5 atm under hydrogen pressure, at a temperature of 0 to 200 ° C, preferably 2 ° C. Incubate at 800 ° for 0.5 hours for 10 hours. Purification and isolation of the target substance are performed by a conventional method.
- the pyridovirimidine derivative represented by the general formula [I-] according to the present invention can also be obtained by acid-decomposing the pyridobilimidine derivative represented by the general formula [I-IV].
- the formula [I-II] examples of the aralkyl carbonyl group and the acyl group represented by? Include those listed in? 7 .
- Examples of the acid used in this method include sulfuric acid, SCI (gas), Ox Br (gas), and the like. These acids are used in an amount of 1% for the compound of the formula [I- ⁇ ].
- Water 100-fold molar use, water, methanol, ethanol, dioxane, THF-pense, benzene, tonolenene, xylene, formic acid, acetic acid, pulp.
- the reaction is carried out in a solvent such as ononic acid at a temperature of 0 to 10 CTC, preferably 2 (3 to 5 CTC) for 0.5 to 10 hours. After the reaction, the desired product is purified and isolated by the method shown in the Examples.
- the pyridopyrimidine derivative represented by the general formula [IV] according to the present invention is a compound represented by the general formula [V].
- the compound can be produced by reacting a lidopyrimidine derivative with a compound represented by the general formula [I:].
- the pyridopyrimidine derivative of the general formula [V] can be produced in accordance with the method described in the present invention [Production invention. 1].
- R 8 is chlorine, odor mottle which halogen, main butoxy group, Puroho 0 Kin group, a lower alkoxy group such as Isopurobokishi group, methyl substituted by the a phenyl group which may optionally be nucleus-substituted by a two preparative port group Group, for example, specifically, a benzyl group, a J) -chlorophenylmethyl group, a p-methoxyphenylmethyl group or hydrogen, and preferably a benzyl group or hydrogen.
- a two preparative port group Group for example, specifically, a benzyl group, a J) -chlorophenylmethyl group, a p-methoxyphenylmethyl group or hydrogen, and preferably a benzyl group or hydrogen.
- examples of the compound represented by the general formula [M] include lower alkoxycarbonyl groups and aralkyloxycarbonyl groups listed as 7 .
- reaction solvent aromatic hydrocarbons such as benzene, toluene and xylene, and ethers such as dioxane can be used, and preferably ⁇ .
- the substance has excellent activity as a herbicide. That is, the present substance can be used as a paddy field and upland herbicide.
- the weeds targeted by herbicides are especially effective against paddy field weeds, tamagayari, scallops, fireflies, spatula, and other upland weeds such as paddy weeds, hie, mexispa, aobu and kogomekaari.
- the substance of the present invention alone or a mixture of the substance with a body, a surfactant, a dispersant, an auxiliary agent and the like is formulated into a wettable powder, an emulsion, a fine particle or a granule. Dilute to an appropriate concentration and spray or apply directly.
- Na-sodium sodium 240 (0% in oil, 6 dishes 0 I) was washed with hexane and suspended in iV-dimethylformamide (Di) 5 / ⁇ . Then, 2 - dimethyl Ryomi Bruno - N - Echiru - 4 - Mechiruhi 0 Li Mi di emissions - 5 - Karubonami de 1. 0 4 g of (5 mm o I) of the i solution ⁇ Q nd) was added, 1 5 The reaction was performed at 0 ° C for 1.5 hours. F is distilled off under reduced pressure and then water 0 was added and extracted with ethyl acetate.
- Example 2 ⁇ -ethyl-2- (1-hydroxyperidinyl) pyridine [4,5-d .] arsenide Li Mi Jin - 5 (O) - sign yield: 0 7% mp: 1 5 1 ⁇ 1 5 2 ° C infrared absorption spectrum (S ⁇ tablets; - 1) 1 0 5 5 1 0 2 2, 1 5 7 5
- Field soil was packed into porcelain pots with an inner diameter of 9 cm, and Aobu, Kogome and Ryari were sown. Immediately, 300 g of a wettable powder containing the specified compound per 1 are dispersed in 20 liters of water, and sprayed over the entire surface of the soil with a small sprayer from above the pot. After the treatment, the plants were placed in a greenhouse for one day and the herbicidal efficacy was examined.
- novel compounds of the present invention are useful as herbicides c
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- Chemical & Material Sciences (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59/163772 | 1984-08-06 | ||
| JP59163772A JPS6143190A (ja) | 1984-08-06 | 1984-08-06 | ピリドピリミジン誘導体およびその製法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1986001207A1 true WO1986001207A1 (en) | 1986-02-27 |
Family
ID=15780422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP1985/000441 WO1986001207A1 (en) | 1984-08-06 | 1985-08-06 | Pyridopyrimidine derivatives and process for their preparation |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS6143190A (enrdf_load_stackoverflow) |
| WO (1) | WO1986001207A1 (enrdf_load_stackoverflow) |
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| CN102399225A (zh) * | 2011-11-28 | 2012-04-04 | 江西师范大学 | 具有除草活性的3-含氟取代苯甲酰胺基-3,4-二氢-4-亚胺-5-甲硫基-7-乙硫基嘧啶并[4,5-d]嘧啶及其制备方法 |
| CN102491977A (zh) * | 2011-11-28 | 2012-06-13 | 江西师范大学 | 具有除草活性的1-取代苯氧亚甲基-8-烷硫基-10-甲硫基嘧啶并[5,4-e]-1,2,三唑并[1,5-c]嘧啶及制备方法 |
| WO2018140600A1 (en) * | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | Fused hetero-hetero bicyclic compounds and methods of use thereof |
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| CN110382483A (zh) * | 2017-01-26 | 2019-10-25 | 亚瑞克西斯制药公司 | 稠合的n-杂环化合物及其使用方法 |
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- 1984-08-06 JP JP59163772A patent/JPS6143190A/ja active Granted
-
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- 1985-08-06 WO PCT/JP1985/000441 patent/WO1986001207A1/ja unknown
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| CN102491977A (zh) * | 2011-11-28 | 2012-06-13 | 江西师范大学 | 具有除草活性的1-取代苯氧亚甲基-8-烷硫基-10-甲硫基嘧啶并[5,4-e]-1,2,三唑并[1,5-c]嘧啶及制备方法 |
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Also Published As
| Publication number | Publication date |
|---|---|
| JPH0339508B2 (enrdf_load_stackoverflow) | 1991-06-14 |
| JPS6143190A (ja) | 1986-03-01 |
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