AP503A - Insecticidal 5-substituted-2,4-diaminopyrimidine derivatives. - Google Patents
Insecticidal 5-substituted-2,4-diaminopyrimidine derivatives. Download PDFInfo
- Publication number
- AP503A AP503A APAP/P/1993/000595A AP9300595A AP503A AP 503 A AP503 A AP 503A AP 9300595 A AP9300595 A AP 9300595A AP 503 A AP503 A AP 503A
- Authority
- AP
- ARIPO
- Prior art keywords
- hydrogen
- grams
- mole
- lower alkyl
- phenyl
- Prior art date
Links
- -1 5-substituted-2,4-diaminopyrimidine Chemical class 0.000 title claims abstract description 77
- 230000000749 insecticidal effect Effects 0.000 title claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 158
- 239000001257 hydrogen Substances 0.000 claims abstract description 91
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 91
- 239000000203 mixture Substances 0.000 claims abstract description 91
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 85
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 35
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 150000001343 alkyl silanes Chemical class 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 53
- 241000238631 Hexapoda Species 0.000 claims description 46
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
- 150000002431 hydrogen Chemical class 0.000 claims description 40
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical group 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000001188 haloalkyl group Chemical group 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 125000004385 trihaloalkyl group Chemical group 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 239000002917 insecticide Substances 0.000 claims description 8
- 229910052720 vanadium Inorganic materials 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 2
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 2
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 2
- 125000005592 polycycloalkyl group Polymers 0.000 abstract description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 140
- 230000015572 biosynthetic process Effects 0.000 description 134
- 238000003786 synthesis reaction Methods 0.000 description 132
- 239000011541 reaction mixture Substances 0.000 description 128
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 107
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 97
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 89
- 239000000543 intermediate Substances 0.000 description 85
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 81
- 239000000243 solution Substances 0.000 description 79
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 70
- 238000012360 testing method Methods 0.000 description 60
- 239000000460 chlorine Substances 0.000 description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 48
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 44
- 239000007787 solid Substances 0.000 description 43
- 239000000706 filtrate Substances 0.000 description 38
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 37
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 35
- 239000003921 oil Substances 0.000 description 34
- 235000019198 oils Nutrition 0.000 description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 26
- 230000009036 growth inhibition Effects 0.000 description 26
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- 229910000027 potassium carbonate Inorganic materials 0.000 description 24
- 239000012299 nitrogen atmosphere Substances 0.000 description 23
- 239000000741 silica gel Substances 0.000 description 23
- 229910002027 silica gel Inorganic materials 0.000 description 23
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 22
- 235000019341 magnesium sulphate Nutrition 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- 238000010992 reflux Methods 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 20
- 229960000789 guanidine hydrochloride Drugs 0.000 description 20
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 20
- 239000000126 substance Substances 0.000 description 20
- 238000004440 column chromatography Methods 0.000 description 19
- 235000005911 diet Nutrition 0.000 description 19
- 230000037213 diet Effects 0.000 description 19
- 238000010828 elution Methods 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000000284 extract Substances 0.000 description 18
- 238000001914 filtration Methods 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 15
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 15
- 241000256244 Heliothis virescens Species 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 239000003208 petroleum Substances 0.000 description 14
- 150000003230 pyrimidines Chemical class 0.000 description 14
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 13
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 description 11
- 230000012010 growth Effects 0.000 description 11
- 239000010410 layer Substances 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000012141 concentrate Substances 0.000 description 10
- 235000008504 concentrate Nutrition 0.000 description 10
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 10
- RFYFPICRESHAJC-UHFFFAOYSA-N 1-(3-iodopropyl)naphthalene Chemical compound C1=CC=C2C(CCCI)=CC=CC2=C1 RFYFPICRESHAJC-UHFFFAOYSA-N 0.000 description 9
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- HUPVIAINOSTNBJ-HWKANZROSA-N (e)-3-ethoxyprop-2-enenitrile Chemical compound CCO\C=C\C#N HUPVIAINOSTNBJ-HWKANZROSA-N 0.000 description 8
- KLFCTZBLVSRWSW-UHFFFAOYSA-N 5-(2-ethylbutoxy)pyrimidine-2,4-diamine Chemical compound CCC(CC)COC1=CN=C(N)N=C1N KLFCTZBLVSRWSW-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
- MIZKXHBNFZFLJP-UHFFFAOYSA-N 3-(3-phenylphenyl)propanenitrile Chemical compound N#CCCC1=CC=CC(C=2C=CC=CC=2)=C1 MIZKXHBNFZFLJP-UHFFFAOYSA-N 0.000 description 7
- JUUBFXIMFOJFOF-UHFFFAOYSA-N 5-(4-chloro-3-nitrophenyl)-6-ethylpyrimidine-2,4-diamine Chemical compound CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C([N+]([O-])=O)=C1 JUUBFXIMFOJFOF-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 239000000969 carrier Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical class NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- HWIKMSXIILZULT-UHFFFAOYSA-N 3-undecylphenol Chemical compound CCCCCCCCCCCC1=CC=CC(O)=C1 HWIKMSXIILZULT-UHFFFAOYSA-N 0.000 description 6
- XOMGENVDQWACIS-UHFFFAOYSA-N 5-(1-adamantyl)-6-methylpyrimidine-2,4-diamine Chemical compound CC1=NC(N)=NC(N)=C1C1(C2)CC(C3)CC2CC3C1 XOMGENVDQWACIS-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 241000256247 Spodoptera exigua Species 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 6
- 229940058936 antimalarials diaminopyrimidines Drugs 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 241000255993 Trichoplusia ni Species 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- GEMFOQNVIPGLNR-UHFFFAOYSA-N ethyl 2-chloro-3-oxopentanoate Chemical compound CCOC(=O)C(Cl)C(=O)CC GEMFOQNVIPGLNR-UHFFFAOYSA-N 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000009518 sodium iodide Nutrition 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000012258 stirred mixture Substances 0.000 description 5
- CIBJFCTWGISUNT-UHFFFAOYSA-N 2,4-diamino-6-methylpyrimidin-5-ol Chemical compound CC1=NC(N)=NC(N)=C1O CIBJFCTWGISUNT-UHFFFAOYSA-N 0.000 description 4
- UAPRJTNYAWRHDW-UHFFFAOYSA-N 2-(3-naphthalen-1-ylpropyl)propanedinitrile Chemical compound C1=CC=C2C(CCCC(C#N)C#N)=CC=CC2=C1 UAPRJTNYAWRHDW-UHFFFAOYSA-N 0.000 description 4
- GXDIYRDULOYYKH-UHFFFAOYSA-N 2-(ethoxymethylidene)-5-naphthalen-1-ylpentanenitrile Chemical compound C1=CC=C2C(CCCC(=COCC)C#N)=CC=CC2=C1 GXDIYRDULOYYKH-UHFFFAOYSA-N 0.000 description 4
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
- DLMMQGKUUAUGLZ-UHFFFAOYSA-N 5-(3-phenylphenyl)pentanenitrile Chemical compound N#CCCCCC1=CC=CC(C=2C=CC=CC=2)=C1 DLMMQGKUUAUGLZ-UHFFFAOYSA-N 0.000 description 4
- XVWFUIITDRRLLC-UHFFFAOYSA-N 5-hydroxy-5-[3-(trifluoromethyl)phenyl]hexanenitrile Chemical compound N#CCCCC(O)(C)C1=CC=CC(C(F)(F)F)=C1 XVWFUIITDRRLLC-UHFFFAOYSA-N 0.000 description 4
- AHGQXRKGVYOSKC-UHFFFAOYSA-N 6-ethyl-5-[3-(2,4,5-trichlorophenyl)propyl]pyrimidine-2,4-diamine Chemical compound CCC1=NC(N)=NC(N)=C1CCCC1=CC(Cl)=C(Cl)C=C1Cl AHGQXRKGVYOSKC-UHFFFAOYSA-N 0.000 description 4
- ROOWPYZRTUQRAH-UHFFFAOYSA-N 6-methyl-5-[3-[2-(trifluoromethyl)phenyl]propyl]pyrimidine-2,4-diamine Chemical compound CC1=NC(N)=NC(N)=C1CCCC1=CC=CC=C1C(F)(F)F ROOWPYZRTUQRAH-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- QCHDRUGIAZBPGB-UHFFFAOYSA-N ethyl 5-phenylpentanoate Chemical compound CCOC(=O)CCCCC1=CC=CC=C1 QCHDRUGIAZBPGB-UHFFFAOYSA-N 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- FTBCLVNCUGMATM-UHFFFAOYSA-N n-[2-chloro-5-(2,4-diamino-6-ethylpyrimidin-5-yl)phenyl]undecanamide Chemical compound C1=C(Cl)C(NC(=O)CCCCCCCCCC)=CC(C=2C(=NC(N)=NC=2N)CC)=C1 FTBCLVNCUGMATM-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229910052727 yttrium Inorganic materials 0.000 description 4
- SVDBTUSIRHAUET-UHFFFAOYSA-N (2,4-diamino-6-methylpyrimidin-5-yl) sulfate;hydron Chemical compound CC1=NC(N)=NC(N)=C1OS(O)(=O)=O SVDBTUSIRHAUET-UHFFFAOYSA-N 0.000 description 3
- RGYVDOAMWQKART-UHFFFAOYSA-N (2,4-diaminopyrimidin-5-yl) sulfate;hydron Chemical compound NC1=NC=C(OS(O)(=O)=O)C(N)=N1 RGYVDOAMWQKART-UHFFFAOYSA-N 0.000 description 3
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 3
- CBOXHDINFLNKOX-UHFFFAOYSA-N 1-(3-bromopropoxy)-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1OCCCBr CBOXHDINFLNKOX-UHFFFAOYSA-N 0.000 description 3
- QSAFBABZCQWYNA-UHFFFAOYSA-N 1-(3-iodopropyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCCI)C=C1 QSAFBABZCQWYNA-UHFFFAOYSA-N 0.000 description 3
- RTFPTPXBTIUISM-UHFFFAOYSA-N 1-(bromomethyl)-3-phenylbenzene Chemical compound BrCC1=CC=CC(C=2C=CC=CC=2)=C1 RTFPTPXBTIUISM-UHFFFAOYSA-N 0.000 description 3
- HVWZMGZBJCJDOX-UHFFFAOYSA-N 1-bromo-3-phenylmethoxybenzene Chemical compound BrC1=CC=CC(OCC=2C=CC=CC=2)=C1 HVWZMGZBJCJDOX-UHFFFAOYSA-N 0.000 description 3
- YAZOSWYXGIILIV-UHFFFAOYSA-N 2-(1-methoxypropylidene)-5-[3-(trifluoromethyl)phenyl]hexanenitrile Chemical compound CCC(OC)=C(C#N)CCC(C)C1=CC=CC(C(F)(F)F)=C1 YAZOSWYXGIILIV-UHFFFAOYSA-N 0.000 description 3
- AGXLQHPRJDFLAW-UHFFFAOYSA-N 2-(ethoxymethylidene)-5-(4-methoxyphenyl)pentanenitrile Chemical compound CCOC=C(C#N)CCCC1=CC=C(OC)C=C1 AGXLQHPRJDFLAW-UHFFFAOYSA-N 0.000 description 3
- MPTCCEZZUSEMNC-UHFFFAOYSA-N 2-(ethoxymethylidene)-7-naphthalen-1-ylheptanenitrile Chemical compound C1=CC=C2C(CCCCCC(=COCC)C#N)=CC=CC2=C1 MPTCCEZZUSEMNC-UHFFFAOYSA-N 0.000 description 3
- PDLSSWRRHUOBCC-UHFFFAOYSA-N 2-(hydroxymethylidene)-6-phenylhexanenitrile Chemical compound OC=C(C#N)CCCCC1=CC=CC=C1 PDLSSWRRHUOBCC-UHFFFAOYSA-N 0.000 description 3
- CFQFWMRUJPSKBW-UHFFFAOYSA-N 2-acetyl-5-[2-(trifluoromethyl)phenyl]pentanenitrile Chemical compound CC(=O)C(C#N)CCCC1=CC=CC=C1C(F)(F)F CFQFWMRUJPSKBW-UHFFFAOYSA-N 0.000 description 3
- KDQURFMHSVKIAP-UHFFFAOYSA-N 3-(3-phenylphenyl)prop-2-enenitrile Chemical compound N#CC=CC1=CC=CC(C=2C=CC=CC=2)=C1 KDQURFMHSVKIAP-UHFFFAOYSA-N 0.000 description 3
- KKGUMGWNFARLSL-UHFFFAOYSA-N 3-(bromomethyl)pentane Chemical compound CCC(CC)CBr KKGUMGWNFARLSL-UHFFFAOYSA-N 0.000 description 3
- LBIRYFNUKUDUJV-UHFFFAOYSA-N 3-hydroxy-3-(3-phenylphenyl)propanenitrile Chemical compound N#CCC(O)C1=CC=CC(C=2C=CC=CC=2)=C1 LBIRYFNUKUDUJV-UHFFFAOYSA-N 0.000 description 3
- DVZQYGZEAFWYTK-UHFFFAOYSA-N 3-methoxy-2-[(3-phenylphenyl)methyl]pent-2-enenitrile Chemical compound CCC(OC)=C(C#N)CC1=CC=CC(C=2C=CC=CC=2)=C1 DVZQYGZEAFWYTK-UHFFFAOYSA-N 0.000 description 3
- IZYBVBNOENNJNW-UHFFFAOYSA-N 3-methoxy-2-[3-(2,4,5-trichlorophenyl)propyl]pent-2-enenitrile Chemical compound CCC(OC)=C(C#N)CCCC1=CC(Cl)=C(Cl)C=C1Cl IZYBVBNOENNJNW-UHFFFAOYSA-N 0.000 description 3
- ULZOICXIHIAYQY-UHFFFAOYSA-N 3-methoxy-7-phenyl-2-(5-phenylpentyl)hept-2-enenitrile Chemical compound C=1C=CC=CC=1CCCCCC(C#N)=C(OC)CCCCC1=CC=CC=C1 ULZOICXIHIAYQY-UHFFFAOYSA-N 0.000 description 3
- LSYAESHKCVOHFC-UHFFFAOYSA-N 3-naphthalen-1-ylpropan-1-ol Chemical compound C1=CC=C2C(CCCO)=CC=CC2=C1 LSYAESHKCVOHFC-UHFFFAOYSA-N 0.000 description 3
- HSIDYYCWEHGCSV-UHFFFAOYSA-N 3-naphthalen-1-ylpropyl methanesulfonate Chemical compound C1=CC=C2C(CCCOS(=O)(=O)C)=CC=CC2=C1 HSIDYYCWEHGCSV-UHFFFAOYSA-N 0.000 description 3
- KUHYUBLQGOJRNM-UHFFFAOYSA-N 3-oxo-2-[3-(2,4,5-trichlorophenyl)propyl]pentanenitrile Chemical compound CCC(=O)C(C#N)CCCC1=CC(Cl)=C(Cl)C=C1Cl KUHYUBLQGOJRNM-UHFFFAOYSA-N 0.000 description 3
- YPVLTVILLOUPEI-UHFFFAOYSA-N 3-oxo-2-[3-(3-phenylphenyl)propyl]pentanenitrile Chemical compound CCC(=O)C(C#N)CCCC1=CC=CC(C=2C=CC=CC=2)=C1 YPVLTVILLOUPEI-UHFFFAOYSA-N 0.000 description 3
- BORKQGSNUMKENR-UHFFFAOYSA-N 3-oxo-7-phenyl-2-(5-phenylpentyl)heptanenitrile Chemical compound C=1C=CC=CC=1CCCCCC(C#N)C(=O)CCCCC1=CC=CC=C1 BORKQGSNUMKENR-UHFFFAOYSA-N 0.000 description 3
- XPZJPWBLMBQDGI-UHFFFAOYSA-N 4-(2,4,5-trichlorophenyl)but-3-yn-1-ol Chemical compound OCCC#CC1=CC(Cl)=C(Cl)C=C1Cl XPZJPWBLMBQDGI-UHFFFAOYSA-N 0.000 description 3
- NXJIGRDYWLLNBX-UHFFFAOYSA-N 5-(1-adamantyl)-2-amino-6-methyl-1h-pyrimidin-4-one Chemical compound CC1=NC(N)=NC(O)=C1C1(C2)CC(C3)CC2CC3C1 NXJIGRDYWLLNBX-UHFFFAOYSA-N 0.000 description 3
- QMOKEASABXBFPL-UHFFFAOYSA-N 5-(2,4,5-trichlorophenyl)pentanenitrile Chemical compound ClC1=CC(Cl)=C(CCCCC#N)C=C1Cl QMOKEASABXBFPL-UHFFFAOYSA-N 0.000 description 3
- FBAZXCGPKSJTCE-UHFFFAOYSA-N 5-(3-amino-4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine Chemical compound CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C(N)=C1 FBAZXCGPKSJTCE-UHFFFAOYSA-N 0.000 description 3
- CEXIBNHBJJKWMZ-UHFFFAOYSA-N 5-(3-naphthalen-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound NC1=NC(N)=NC=C1CCCC1=CC=CC2=CC=CC=C12 CEXIBNHBJJKWMZ-UHFFFAOYSA-N 0.000 description 3
- DLGNUYGVDCLKTH-UHFFFAOYSA-N 5-(4-phenylbutyl)pyrimidine-2,4-diamine Chemical compound NC1=NC(N)=NC=C1CCCCC1=CC=CC=C1 DLGNUYGVDCLKTH-UHFFFAOYSA-N 0.000 description 3
- XIKQJYYQEQWFIL-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]hexanenitrile Chemical compound N#CCCCC(C)C1=CC=CC(C(F)(F)F)=C1 XIKQJYYQEQWFIL-UHFFFAOYSA-N 0.000 description 3
- OSSZOVQAMZRAHQ-UHFFFAOYSA-N 5-[4-chloro-3-(undecylamino)phenyl]-6-ethylpyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(NCCCCCCCCCCC)=CC(C=2C(=NC(N)=NC=2N)CC)=C1 OSSZOVQAMZRAHQ-UHFFFAOYSA-N 0.000 description 3
- IMGMWMATKUWNRK-UHFFFAOYSA-N 5-naphthalen-1-ylpent-4-yn-1-ol Chemical compound C1=CC=C2C(C#CCCCO)=CC=CC2=C1 IMGMWMATKUWNRK-UHFFFAOYSA-N 0.000 description 3
- AYIBDXMQFYAZJF-UHFFFAOYSA-N 5-naphthalen-1-ylpentan-1-ol Chemical compound C1=CC=C2C(CCCCCO)=CC=CC2=C1 AYIBDXMQFYAZJF-UHFFFAOYSA-N 0.000 description 3
- FUVWRUJASRBHEK-UHFFFAOYSA-N 5-phenylpyrimidine-2,4-diamine Chemical compound NC1=NC(N)=NC=C1C1=CC=CC=C1 FUVWRUJASRBHEK-UHFFFAOYSA-N 0.000 description 3
- VQHITFFJBFOMBG-UHFFFAOYSA-N 6-(4-methylpiperazin-1-yl)-11h-benzo[b][1,4]benzodiazepine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=CC=CC=C12 VQHITFFJBFOMBG-UHFFFAOYSA-N 0.000 description 3
- YWXNNXGEZRZHJQ-UHFFFAOYSA-N 6-(4-phenylbutyl)-5-(5-phenylpentyl)pyrimidine-2,4-diamine Chemical compound C=1C=CC=CC=1CCCCC1=NC(N)=NC(N)=C1CCCCCC1=CC=CC=C1 YWXNNXGEZRZHJQ-UHFFFAOYSA-N 0.000 description 3
- BOQULSHFABJIKN-UHFFFAOYSA-N 6-methyl-5-[3-[2-(trifluoromethyl)phenoxy]propoxy]pyrimidine-2,4-diamine Chemical compound CC1=NC(N)=NC(N)=C1OCCCOC1=CC=CC=C1C(F)(F)F BOQULSHFABJIKN-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 244000045195 Cicer arietinum Species 0.000 description 3
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 229910007161 Si(CH3)3 Inorganic materials 0.000 description 3
- RSJUWHRYHDISTK-UHFFFAOYSA-N [1-cyano-4-(3-phenylphenyl)butan-2-yl] methanesulfonate Chemical compound CS(=O)(=O)OC(CC#N)CCC1=CC=CC(C=2C=CC=CC=2)=C1 RSJUWHRYHDISTK-UHFFFAOYSA-N 0.000 description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229960000892 attapulgite Drugs 0.000 description 3
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 3
- 239000004927 clay Substances 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
- 229940043279 diisopropylamine Drugs 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- MSSAFCYKWMNVMZ-UHFFFAOYSA-N ethyl 3-(3-bromophenyl)prop-2-enoate Chemical compound CCOC(=O)C=CC1=CC=CC(Br)=C1 MSSAFCYKWMNVMZ-UHFFFAOYSA-N 0.000 description 3
- RPVHNWBGFZYXRC-UHFFFAOYSA-N ethyl 3-(3-phenylphenyl)propanoate Chemical compound CCOC(=O)CCC1=CC=CC(C=2C=CC=CC=2)=C1 RPVHNWBGFZYXRC-UHFFFAOYSA-N 0.000 description 3
- YREBQYMNCJOFML-UHFFFAOYSA-N ethyl 3-naphthalen-1-ylpropanoate Chemical compound C1=CC=C2C(CCC(=O)OCC)=CC=CC2=C1 YREBQYMNCJOFML-UHFFFAOYSA-N 0.000 description 3
- CMJROYXVBXLTCA-UHFFFAOYSA-N ethyl 3-oxo-2-(3-undecylphenoxy)pentanoate Chemical compound CCCCCCCCCCCC1=CC=CC(OC(C(=O)CC)C(=O)OCC)=C1 CMJROYXVBXLTCA-UHFFFAOYSA-N 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 3
- 229910052625 palygorskite Inorganic materials 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- WKSAUQYGYAYLPV-UHFFFAOYSA-N pyrimethamine Chemical compound CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C=C1 WKSAUQYGYAYLPV-UHFFFAOYSA-N 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
- 235000019345 sodium thiosulphate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000011550 stock solution Substances 0.000 description 3
- 125000000547 substituted alkyl group Chemical group 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- JUKPJGZUFHCZQI-UHFFFAOYSA-N undecanoyl chloride Chemical compound CCCCCCCCCCC(Cl)=O JUKPJGZUFHCZQI-UHFFFAOYSA-N 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- FSWNRRSWFBXQCL-UHFFFAOYSA-N (3-bromophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1 FSWNRRSWFBXQCL-UHFFFAOYSA-N 0.000 description 2
- WGUZZTGZDPJWSG-UHFFFAOYSA-N (3-phenylphenyl)methanol Chemical compound OCC1=CC=CC(C=2C=CC=CC=2)=C1 WGUZZTGZDPJWSG-UHFFFAOYSA-N 0.000 description 2
- BOZQIJPDCKPRBV-MDZDMXLPSA-N (e)-2-cyano-3-[2-(diethylamino)ethylamino]but-2-enamide Chemical compound CCN(CC)CCN\C(C)=C(/C#N)C(N)=O BOZQIJPDCKPRBV-MDZDMXLPSA-N 0.000 description 2
- GLABUMKWRLMDDY-CMDGGOBGSA-N (e)-2-cyano-3-[3-(dimethylamino)propylamino]but-2-enamide Chemical compound CN(C)CCCN\C(C)=C(/C#N)C(N)=O GLABUMKWRLMDDY-CMDGGOBGSA-N 0.000 description 2
- GVSGVBVZXJOLDD-UHFFFAOYSA-N (n'-ethylcarbamimidoyl)azanium;chloride Chemical compound [Cl-].CCN=C(N)[NH3+] GVSGVBVZXJOLDD-UHFFFAOYSA-N 0.000 description 2
- UVLAGCAJWBLZLZ-UHFFFAOYSA-N 1-(3-phenylmethoxyphenyl)undecan-1-ol Chemical compound CCCCCCCCCCC(O)C1=CC=CC(OCC=2C=CC=CC=2)=C1 UVLAGCAJWBLZLZ-UHFFFAOYSA-N 0.000 description 2
- XXBJMLMRXFEMQD-UHFFFAOYSA-N 1-(5-iodopentyl)naphthalene Chemical compound C1=CC=C2C(CCCCCI)=CC=CC2=C1 XXBJMLMRXFEMQD-UHFFFAOYSA-N 0.000 description 2
- YQGHJCYLMLPCCB-UHFFFAOYSA-N 2,4-diaminopyrimidin-5-ol Chemical compound NC1=NC=C(O)C(N)=N1 YQGHJCYLMLPCCB-UHFFFAOYSA-N 0.000 description 2
- OFSDEKNZWPCSPO-UHFFFAOYSA-N 2-(1-methoxyethylidene)-5-[2-(trifluoromethyl)phenyl]pentanenitrile Chemical compound COC(C)=C(C#N)CCCC1=CC=CC=C1C(F)(F)F OFSDEKNZWPCSPO-UHFFFAOYSA-N 0.000 description 2
- OWMYRYCJAQPUQY-UHFFFAOYSA-N 2-(methoxymethylidene)-6-phenylhexanenitrile Chemical compound COC=C(C#N)CCCCC1=CC=CC=C1 OWMYRYCJAQPUQY-UHFFFAOYSA-N 0.000 description 2
- PAYROHWFGZADBR-UHFFFAOYSA-N 2-[[4-amino-5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidin-2-yl]amino]propane-1,3-diol Chemical compound C1=C(I)C(OC)=CC(C(C)C)=C1OC1=CN=C(NC(CO)CO)N=C1N PAYROHWFGZADBR-UHFFFAOYSA-N 0.000 description 2
- GTYQPTJCCKTBDX-UHFFFAOYSA-N 2-amino-6-ethyl-5-(3-undecylphenoxy)-1h-pyrimidin-4-one Chemical compound CCCCCCCCCCCC1=CC=CC(OC=2C(=NC(N)=NC=2O)CC)=C1 GTYQPTJCCKTBDX-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- XBQLMIATEPGBKK-UHFFFAOYSA-N 2-propanoyl-5-[3-(trifluoromethyl)phenyl]hexanenitrile Chemical compound CCC(=O)C(C#N)CCC(C)C1=CC=CC(C(F)(F)F)=C1 XBQLMIATEPGBKK-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- VEOWECQFESDUIY-UHFFFAOYSA-N 3-hydroxy-5-(3-phenylphenyl)pentanenitrile Chemical compound N#CCC(O)CCC1=CC=CC(C=2C=CC=CC=2)=C1 VEOWECQFESDUIY-UHFFFAOYSA-N 0.000 description 2
- VAUKSDRNLWRCID-UHFFFAOYSA-N 3-methoxy-2-[3-(3-phenylphenyl)propyl]pent-2-enenitrile Chemical compound CCC(OC)=C(C#N)CCCC1=CC=CC(C=2C=CC=CC=2)=C1 VAUKSDRNLWRCID-UHFFFAOYSA-N 0.000 description 2
- LYNBOEDEGMIPTK-UHFFFAOYSA-N 3-oxo-2-[(3-phenylphenyl)methyl]pentanenitrile Chemical compound CCC(=O)C(C#N)CC1=CC=CC(C=2C=CC=CC=2)=C1 LYNBOEDEGMIPTK-UHFFFAOYSA-N 0.000 description 2
- FVHAXCALIGBSTL-UHFFFAOYSA-N 3-oxo-5-(3-phenylphenyl)pentanenitrile Chemical compound N#CCC(=O)CCC1=CC=CC(C=2C=CC=CC=2)=C1 FVHAXCALIGBSTL-UHFFFAOYSA-N 0.000 description 2
- KFKSIUOALVIACE-UHFFFAOYSA-N 3-phenylbenzaldehyde Chemical compound O=CC1=CC=CC(C=2C=CC=CC=2)=C1 KFKSIUOALVIACE-UHFFFAOYSA-N 0.000 description 2
- XQGLGERFRMXCAX-UHFFFAOYSA-N 4-(2,4,5-trichlorophenyl)butyl methanesulfonate Chemical compound CS(=O)(=O)OCCCCC1=CC(Cl)=C(Cl)C=C1Cl XQGLGERFRMXCAX-UHFFFAOYSA-N 0.000 description 2
- BEPMXVPDCJISSQ-UHFFFAOYSA-N 5-(1-adamantyl)-4-chloro-6-methylpyrimidin-2-amine;hydrochloride Chemical compound Cl.CC1=NC(N)=NC(Cl)=C1C1(C2)CC(C3)CC2CC3C1 BEPMXVPDCJISSQ-UHFFFAOYSA-N 0.000 description 2
- MZILJZMZCKWMJD-UHFFFAOYSA-N 5-(3-naphthalen-1-ylpropyl)pyrimidine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N)=C1CCCC1=CC=CC2=CC=CC=C12 MZILJZMZCKWMJD-UHFFFAOYSA-N 0.000 description 2
- QIKMZTIMDQZYDZ-UHFFFAOYSA-N 5-(5-naphthalen-1-ylpentyl)pyrimidine-2,4-diamine Chemical compound NC1=NC(N)=NC=C1CCCCCC1=CC=CC2=CC=CC=C12 QIKMZTIMDQZYDZ-UHFFFAOYSA-N 0.000 description 2
- HCGOOYAWYTZZIT-UHFFFAOYSA-N 5-[2-(trifluoromethyl)phenyl]pent-4-ynenitrile Chemical compound FC(F)(F)C1=CC=CC=C1C#CCCC#N HCGOOYAWYTZZIT-UHFFFAOYSA-N 0.000 description 2
- QUQJWHUGGGNJFB-UHFFFAOYSA-N 5-[2-(trifluoromethyl)phenyl]pentanenitrile Chemical compound FC(F)(F)C1=CC=CC=C1CCCCC#N QUQJWHUGGGNJFB-UHFFFAOYSA-N 0.000 description 2
- WWHXCSLYTRDZMT-UHFFFAOYSA-N 5-naphthalen-1-ylpentyl methanesulfonate Chemical compound C1=CC=C2C(CCCCCOS(=O)(=O)C)=CC=CC2=C1 WWHXCSLYTRDZMT-UHFFFAOYSA-N 0.000 description 2
- RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 2
- UDAVYCASXKUVHM-UHFFFAOYSA-N 6-ethyl-5-[3-(3-phenylphenyl)propyl]pyrimidine-2,4-diamine Chemical compound CCC1=NC(N)=NC(N)=C1CCCC1=CC=CC(C=2C=CC=CC=2)=C1 UDAVYCASXKUVHM-UHFFFAOYSA-N 0.000 description 2
- XUUGUMBZSOOHQO-UHFFFAOYSA-N 6-ethyl-5-[3-[3-(trifluoromethyl)phenyl]butyl]pyrimidine-2,4-diamine Chemical compound CCC1=NC(N)=NC(N)=C1CCC(C)C1=CC=CC(C(F)(F)F)=C1 XUUGUMBZSOOHQO-UHFFFAOYSA-N 0.000 description 2
- AZVOSTMEMKRXOX-UHFFFAOYSA-N 6-ethyl-5-[4-(2,4,5-trichlorophenyl)butyl]pyrimidine-2,4-diamine Chemical compound CCC1=NC(N)=NC(N)=C1CCCCC1=CC(Cl)=C(Cl)C=C1Cl AZVOSTMEMKRXOX-UHFFFAOYSA-N 0.000 description 2
- RSWHPXKGJFAXFE-UHFFFAOYSA-N 6-methyl-5-(3-phenylpropoxy)pyrimidine-2,4-diamine Chemical compound CC1=NC(N)=NC(N)=C1OCCCC1=CC=CC=C1 RSWHPXKGJFAXFE-UHFFFAOYSA-N 0.000 description 2
- AQZAQRQEUIUZBW-UHFFFAOYSA-N 6-methyl-5-[3-(2,4,5-trichlorophenyl)propyl]pyrimidine-2,4-diamine Chemical compound CC1=NC(N)=NC(N)=C1CCCC1=CC(Cl)=C(Cl)C=C1Cl AQZAQRQEUIUZBW-UHFFFAOYSA-N 0.000 description 2
- RTSCKDBJHRWMJI-UHFFFAOYSA-N 6-methyl-5-[3-(2-methylphenyl)propyl]pyrimidine-2,4-diamine Chemical compound CC1=CC=CC=C1CCCC1=C(C)N=C(N)N=C1N RTSCKDBJHRWMJI-UHFFFAOYSA-N 0.000 description 2
- HERHQNVDSHUKAK-UHFFFAOYSA-N 6-methylpyrimidine-2,4-diamine Chemical compound CC1=CC(N)=NC(N)=N1 HERHQNVDSHUKAK-UHFFFAOYSA-N 0.000 description 2
- BSJKBXNHLQEFMG-UHFFFAOYSA-N 6-phenylhexanenitrile Chemical compound N#CCCCCCC1=CC=CC=C1 BSJKBXNHLQEFMG-UHFFFAOYSA-N 0.000 description 2
- ZFOBOLWWNQKKTC-UHFFFAOYSA-N 7-phenylheptanenitrile Chemical compound N#CCCCCCCC1=CC=CC=C1 ZFOBOLWWNQKKTC-UHFFFAOYSA-N 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical group OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 2
- 229940126639 Compound 33 Drugs 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 231100000111 LD50 Toxicity 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 235000021405 artificial diet Nutrition 0.000 description 2
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- KJAUPJVVFIJSEI-UHFFFAOYSA-N ethyl 2-(1-adamantyl)-3-oxobutanoate Chemical compound C1C(C2)CC3CC2CC1(C(C(C)=O)C(=O)OCC)C3 KJAUPJVVFIJSEI-UHFFFAOYSA-N 0.000 description 2
- LUZDKQBECCRVIW-UHFFFAOYSA-N ethyl 3-(3-phenylphenyl)prop-2-enoate Chemical compound CCOC(=O)C=CC1=CC=CC(C=2C=CC=CC=2)=C1 LUZDKQBECCRVIW-UHFFFAOYSA-N 0.000 description 2
- UDRCONFHWYGWFI-UHFFFAOYSA-N ethyl 3-oxopentanoate Chemical compound CCOC(=O)CC(=O)CC UDRCONFHWYGWFI-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 229960004198 guanidine Drugs 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 2
- 238000006263 metalation reaction Methods 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 2
- UYDLBVPAAFVANX-UHFFFAOYSA-N octylphenoxy polyethoxyethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCO)C=C1 UYDLBVPAAFVANX-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- CRWVOXFUXPYTRK-UHFFFAOYSA-N pent-4-yn-1-ol Chemical compound OCCCC#C CRWVOXFUXPYTRK-UHFFFAOYSA-N 0.000 description 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 1
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
- PTGWZRUXLZLOJM-UHFFFAOYSA-N (3-phenylphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC(C=2C=CC=CC=2)=C1 PTGWZRUXLZLOJM-UHFFFAOYSA-N 0.000 description 1
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 1
- STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 description 1
- OIIOPWHTJZYKIL-PMACEKPBSA-N (5S)-5-[[[5-[2-chloro-3-[2-chloro-3-[6-methoxy-5-[[[(2S)-5-oxopyrrolidin-2-yl]methylamino]methyl]pyrazin-2-yl]phenyl]phenyl]-3-methoxypyrazin-2-yl]methylamino]methyl]pyrrolidin-2-one Chemical compound C1(=C(N=C(C2=C(C(C3=CC=CC(=C3Cl)C3=NC(OC)=C(N=C3)CNC[C@H]3NC(=O)CC3)=CC=C2)Cl)C=N1)OC)CNC[C@H]1NC(=O)CC1 OIIOPWHTJZYKIL-PMACEKPBSA-N 0.000 description 1
- VUEGYUOUAAVYAS-JGGQBBKZSA-N (6ar,9s,10ar)-9-(dimethylsulfamoylamino)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NS(=O)(=O)N(C)C)=C3C2=CNC3=C1 VUEGYUOUAAVYAS-JGGQBBKZSA-N 0.000 description 1
- YEMUSDCFQUBPAL-SNAWJCMRSA-N (e)-3-(3-bromophenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=CC(Br)=C1 YEMUSDCFQUBPAL-SNAWJCMRSA-N 0.000 description 1
- KKXMBRLCXIPURK-UHFFFAOYSA-N 1,2,4-trichloro-5-iodobenzene Chemical compound ClC1=CC(Cl)=C(I)C=C1Cl KKXMBRLCXIPURK-UHFFFAOYSA-N 0.000 description 1
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- HHWSUBFGPXABQR-UHFFFAOYSA-N 1-(3-iodopropylsulfanyl)-4-propylbenzene Chemical compound C(CC)C1=CC=C(SCCCI)C=C1 HHWSUBFGPXABQR-UHFFFAOYSA-N 0.000 description 1
- OJKQPEBNNOFITI-UHFFFAOYSA-N 1-adamantyl 3-oxobutanoate Chemical compound C1C(C2)CC3CC2CC1(OC(=O)CC(=O)C)C3 OJKQPEBNNOFITI-UHFFFAOYSA-N 0.000 description 1
- NNMBNYHMJRJUBC-UHFFFAOYSA-N 1-bromo-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(Br)=C1 NNMBNYHMJRJUBC-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- IGZGUYVVBABKOY-UHFFFAOYSA-N 1-iodo-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1I IGZGUYVVBABKOY-UHFFFAOYSA-N 0.000 description 1
- NHPPIJMARIVBGU-UHFFFAOYSA-N 1-iodonaphthalene Chemical compound C1=CC=C2C(I)=CC=CC2=C1 NHPPIJMARIVBGU-UHFFFAOYSA-N 0.000 description 1
- BLXSFCHWMBESKV-UHFFFAOYSA-N 1-iodopentane Chemical compound CCCCCI BLXSFCHWMBESKV-UHFFFAOYSA-N 0.000 description 1
- AGZOIXITJLBHAX-UHFFFAOYSA-N 1-pent-1-enylnaphthalene Chemical compound C1=CC=C2C(C=CCCC)=CC=CC2=C1 AGZOIXITJLBHAX-UHFFFAOYSA-N 0.000 description 1
- RJFCFNWLPJRCLR-UHFFFAOYSA-N 1-prop-2-enylnaphthalene Chemical compound C1=CC=C2C(CC=C)=CC=CC2=C1 RJFCFNWLPJRCLR-UHFFFAOYSA-N 0.000 description 1
- VTSWSQGDJQFXHB-UHFFFAOYSA-N 2,4,6-trichloro-5-methylpyrimidine Chemical compound CC1=C(Cl)N=C(Cl)N=C1Cl VTSWSQGDJQFXHB-UHFFFAOYSA-N 0.000 description 1
- MOCUUAKIHQAFFV-UHFFFAOYSA-N 2-(1-methoxyethylidene)-5-(2,4,5-trichlorophenyl)pentanenitrile Chemical compound COC(C)=C(C#N)CCCC1=CC(Cl)=C(Cl)C=C1Cl MOCUUAKIHQAFFV-UHFFFAOYSA-N 0.000 description 1
- HDOFOQVVMGWPGJ-UHFFFAOYSA-N 2-(1-methoxyethylidene)-5-(2,4,5-trimethylphenyl)pentanenitrile Chemical compound COC(C)=C(C#N)CCCC1=CC(C)=C(C)C=C1C HDOFOQVVMGWPGJ-UHFFFAOYSA-N 0.000 description 1
- ZYCGYDCGFKPIEO-UHFFFAOYSA-N 2-(1-methoxyethylidene)-5-(2-methylphenyl)pentanenitrile Chemical compound COC(C)=C(C#N)CCCC1=CC=CC=C1C ZYCGYDCGFKPIEO-UHFFFAOYSA-N 0.000 description 1
- MIRIATOKRBBEIJ-UHFFFAOYSA-N 2-(1-methoxyethylidene)-5-(4-methylphenyl)pentanenitrile Chemical compound COC(C)=C(C#N)CCCC1=CC=C(C)C=C1 MIRIATOKRBBEIJ-UHFFFAOYSA-N 0.000 description 1
- RNKJDXRGUAGHTQ-UHFFFAOYSA-N 2-(1-methoxypropylidene)-5-[4-(trifluoromethyl)phenyl]hexanenitrile Chemical compound CCC(OC)=C(C#N)CCC(C)C1=CC=C(C(F)(F)F)C=C1 RNKJDXRGUAGHTQ-UHFFFAOYSA-N 0.000 description 1
- IBHQIODQNHISME-UHFFFAOYSA-N 2-(1-methoxypropylidene)-6-(2,4,5-trichlorophenyl)hexanenitrile Chemical compound CCC(OC)=C(C#N)CCCCC1=CC(Cl)=C(Cl)C=C1Cl IBHQIODQNHISME-UHFFFAOYSA-N 0.000 description 1
- MQPUAVYKVIHUJP-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)ethanamine Chemical compound NCCC1=CC=C(Cl)C(Cl)=C1 MQPUAVYKVIHUJP-UHFFFAOYSA-N 0.000 description 1
- VDWVOAMDJZJHKM-UHFFFAOYSA-N 2-(3-phenylphenyl)pent-2-enenitrile Chemical compound C1(=CC=CC=C1)C=1C=C(C=CC=1)C(C#N)=CCC VDWVOAMDJZJHKM-UHFFFAOYSA-N 0.000 description 1
- YWUYESWISXRSOQ-UHFFFAOYSA-N 2-(3-undecylphenoxy)pyrimidine Chemical compound C(CCCCCCCCCC)C=1C=C(OC2=NC=CC=N2)C=CC=1 YWUYESWISXRSOQ-UHFFFAOYSA-N 0.000 description 1
- ZOQOPXVJANRGJZ-UHFFFAOYSA-N 2-(trifluoromethyl)phenol Chemical compound OC1=CC=CC=C1C(F)(F)F ZOQOPXVJANRGJZ-UHFFFAOYSA-N 0.000 description 1
- YQNRVGJCPCNMKT-LFVJCYFKSA-N 2-[(e)-[[2-(4-benzylpiperazin-1-ium-1-yl)acetyl]hydrazinylidene]methyl]-6-prop-2-enylphenolate Chemical compound [O-]C1=C(CC=C)C=CC=C1\C=N\NC(=O)C[NH+]1CCN(CC=2C=CC=CC=2)CC1 YQNRVGJCPCNMKT-LFVJCYFKSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- KTHVDIQJNOLJBC-UHFFFAOYSA-N 2-[3-(2,4-dichlorophenyl)butyl]-4-methylpyrimidine Chemical compound ClC1=C(C=CC(=C1)Cl)C(CCC1=NC(=CC=N1)C)C KTHVDIQJNOLJBC-UHFFFAOYSA-N 0.000 description 1
- LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 1
- OHFVPBGSKPYIED-UHFFFAOYSA-N 2-methylpyrimidin-5-ol Chemical compound CC1=NC=C(O)C=N1 OHFVPBGSKPYIED-UHFFFAOYSA-N 0.000 description 1
- MZUUDUUUSZHCGF-UHFFFAOYSA-N 2-n-ethyl-5-(3-naphthalen-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound NC1=NC(NCC)=NC=C1CCCC1=CC=CC2=CC=CC=C12 MZUUDUUUSZHCGF-UHFFFAOYSA-N 0.000 description 1
- LCRCBXLHWTVPEQ-UHFFFAOYSA-N 2-phenylbenzaldehyde Chemical compound O=CC1=CC=CC=C1C1=CC=CC=C1 LCRCBXLHWTVPEQ-UHFFFAOYSA-N 0.000 description 1
- KSFORUTXEPGVOW-UHFFFAOYSA-N 2-phenylpyrimidin-4-amine Chemical compound NC1=CC=NC(C=2C=CC=CC=2)=N1 KSFORUTXEPGVOW-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- NIIDHUCLROLCBU-UHFFFAOYSA-N 3-(4-methoxyphenyl)propan-1-ol Chemical compound COC1=CC=C(CCCO)C=C1 NIIDHUCLROLCBU-UHFFFAOYSA-N 0.000 description 1
- VDKZGONUAHUVJF-UHFFFAOYSA-N 3-(dimethylamino)-2-phenylprop-2-enenitrile Chemical compound CN(C)C=C(C#N)C1=CC=CC=C1 VDKZGONUAHUVJF-UHFFFAOYSA-N 0.000 description 1
- BGAJNPLDJJBRHK-UHFFFAOYSA-N 3-[2-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,3,4-thiadiazol-2-yl]-3-methyl-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NN=C(N2C(=C3CN(CCC(O)=O)CCC3=N2)C)S1 BGAJNPLDJJBRHK-UHFFFAOYSA-N 0.000 description 1
- SUISZCALMBHJQX-UHFFFAOYSA-N 3-bromobenzaldehyde Chemical compound BrC1=CC=CC(C=O)=C1 SUISZCALMBHJQX-UHFFFAOYSA-N 0.000 description 1
- MNOJRWOWILAHAV-UHFFFAOYSA-N 3-bromophenol Chemical compound OC1=CC=CC(Br)=C1 MNOJRWOWILAHAV-UHFFFAOYSA-N 0.000 description 1
- XMZQWZJMTBCUFT-UHFFFAOYSA-N 3-bromopropylbenzene Chemical compound BrCCCC1=CC=CC=C1 XMZQWZJMTBCUFT-UHFFFAOYSA-N 0.000 description 1
- PRLKVVMRQFFIOQ-UHFFFAOYSA-N 3-naphthalen-1-ylpropanoic acid Chemical compound C1=CC=C2C(CCC(=O)O)=CC=CC2=C1 PRLKVVMRQFFIOQ-UHFFFAOYSA-N 0.000 description 1
- XOWUZTAOYVTRKO-UHFFFAOYSA-N 3-oxo-2-pentylheptanenitrile Chemical compound C(#N)C(C(CCCC)=O)CCCCC XOWUZTAOYVTRKO-UHFFFAOYSA-N 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HMPIBMDIIZYHSE-UHFFFAOYSA-N 4-(2,4,5-trichlorophenyl)butan-1-ol Chemical compound OCCCCC1=CC(Cl)=C(Cl)C=C1Cl HMPIBMDIIZYHSE-UHFFFAOYSA-N 0.000 description 1
- GEXGQNNXRUCZQW-UHFFFAOYSA-N 4-chloro-6-ethyl-5-(3-undecylphenoxy)pyrimidin-2-amine Chemical compound CCCCCCCCCCCC1=CC=CC(OC=2C(=NC(N)=NC=2Cl)CC)=C1 GEXGQNNXRUCZQW-UHFFFAOYSA-N 0.000 description 1
- SDEBYHVDMCQKNZ-UHFFFAOYSA-N 4-methoxy-6-piperazin-1-ylpyrimidine;hydrochloride Chemical compound Cl.C1=NC(OC)=CC(N2CCNCC2)=N1 SDEBYHVDMCQKNZ-UHFFFAOYSA-N 0.000 description 1
- BOPZDXATCGECMU-UHFFFAOYSA-N 4-n-[2-(4-aminoanilino)ethyl]benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NCCNC1=CC=C(N)C=C1 BOPZDXATCGECMU-UHFFFAOYSA-N 0.000 description 1
- GIDKRAVYSDBCAS-UHFFFAOYSA-N 4-nitro-2-phenylpyrimidine Chemical compound [O-][N+](=O)C1=CC=NC(C=2C=CC=CC=2)=N1 GIDKRAVYSDBCAS-UHFFFAOYSA-N 0.000 description 1
- ZUEOZCBPTFMWGI-UHFFFAOYSA-N 4-oxohexanenitrile Chemical compound CCC(=O)CCC#N ZUEOZCBPTFMWGI-UHFFFAOYSA-N 0.000 description 1
- CRPLAZVDAVITGO-UHFFFAOYSA-N 5-(2,4-dichlorophenyl)-2-(1-methoxyethylidene)hexanenitrile Chemical compound COC(C)=C(C#N)CCC(C)C1=CC=C(Cl)C=C1Cl CRPLAZVDAVITGO-UHFFFAOYSA-N 0.000 description 1
- ZAKNIUOVPZMGSP-UHFFFAOYSA-N 5-(2,4-dichlorophenyl)-2-(1-methoxyethylidene)pentanenitrile Chemical compound COC(C)=C(C#N)CCCC1=CC=C(Cl)C=C1Cl ZAKNIUOVPZMGSP-UHFFFAOYSA-N 0.000 description 1
- LQULALNSGDSCSU-UHFFFAOYSA-N 5-(2-ethylbutoxy)-6-methylpyrimidine-2,4-diamine Chemical compound CCC(CC)COC1=C(C)N=C(N)N=C1N LQULALNSGDSCSU-UHFFFAOYSA-N 0.000 description 1
- DPZMVZIQRMVBBW-UHFFFAOYSA-N 5-Phenyl-1-pentanol Chemical compound OCCCCCC1=CC=CC=C1 DPZMVZIQRMVBBW-UHFFFAOYSA-N 0.000 description 1
- JRWMGULFVUJVTH-UHFFFAOYSA-N 5-[(3-phenylphenyl)methyl]pyrimidine-2,4-diamine Chemical compound NC1=NC(N)=NC=C1CC1=CC=CC(C=2C=CC=CC=2)=C1 JRWMGULFVUJVTH-UHFFFAOYSA-N 0.000 description 1
- AGCIUWGZGASLBP-UHFFFAOYSA-N 5-[3-(2,4-dichlorophenyl)butyl]-6-methylpyrimidine-2,4-diamine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(C)CCC1=C(C)N=C(N)N=C1N AGCIUWGZGASLBP-UHFFFAOYSA-N 0.000 description 1
- PSPLUCCWMZSIQG-UHFFFAOYSA-N 5-[3-(4,4-dichlorocyclohexa-1,5-dien-1-yl)propyl]-6-methylpyrimidine-2,4-diamine Chemical compound CC1=NC(N)=NC(N)=C1CCCC1=CCC(Cl)(Cl)C=C1 PSPLUCCWMZSIQG-UHFFFAOYSA-N 0.000 description 1
- SARONNFAZIWMQW-UHFFFAOYSA-N 5-[3-(4-methoxyphenyl)propyl]-2h-pyrimidine-1,4-diamine Chemical compound C1=CC(OC)=CC=C1CCCC1=CN(N)CN=C1N SARONNFAZIWMQW-UHFFFAOYSA-N 0.000 description 1
- SZRFVBPPAMWZDK-UHFFFAOYSA-N 5-[4-(4-chlorophenyl)butyl]pyrimidine-2,4-diamine Chemical compound NC1=NC(N)=NC=C1CCCCC1=CC=C(Cl)C=C1 SZRFVBPPAMWZDK-UHFFFAOYSA-N 0.000 description 1
- PHSFDXSFHALXMN-UHFFFAOYSA-N 5-[4-[(3,4-dichlorophenyl)methylamino]-3-nitrophenyl]-6-ethylpyrimidine-2,4-diamine Chemical compound CCC1=NC(N)=NC(N)=C1C(C=C1[N+]([O-])=O)=CC=C1NCC1=CC=C(Cl)C(Cl)=C1 PHSFDXSFHALXMN-UHFFFAOYSA-N 0.000 description 1
- TWGNOYAGHYUFFR-UHFFFAOYSA-N 5-methylpyrimidine Chemical compound CC1=CN=CN=C1 TWGNOYAGHYUFFR-UHFFFAOYSA-N 0.000 description 1
- AEVMBQIIZGKQRB-UHFFFAOYSA-N 5-oxohexanenitrile Chemical compound CC(=O)CCCC#N AEVMBQIIZGKQRB-UHFFFAOYSA-N 0.000 description 1
- BYHDDXPKOZIZRV-UHFFFAOYSA-N 5-phenylpentanoic acid Chemical compound OC(=O)CCCCC1=CC=CC=C1 BYHDDXPKOZIZRV-UHFFFAOYSA-N 0.000 description 1
- BZJBRCXUKRLFHV-UHFFFAOYSA-N 5-phenylpentyl methanesulfonate Chemical compound CS(=O)(=O)OCCCCCC1=CC=CC=C1 BZJBRCXUKRLFHV-UHFFFAOYSA-N 0.000 description 1
- RQBQSHOUUKLZLM-UHFFFAOYSA-N 6-(4-chlorophenyl)-2-(ethoxymethylidene)hexanenitrile Chemical compound CCOC=C(C#N)CCCCC1=CC=C(Cl)C=C1 RQBQSHOUUKLZLM-UHFFFAOYSA-N 0.000 description 1
- JCUOLNHGQQXLPO-UHFFFAOYSA-N 6-ethyl-5-(3-undecylphenoxy)pyrimidine-2,4-diamine Chemical compound CCCCCCCCCCCC1=CC=CC(OC=2C(=NC(N)=NC=2N)CC)=C1 JCUOLNHGQQXLPO-UHFFFAOYSA-N 0.000 description 1
- INGMERNHEAWFCU-UHFFFAOYSA-N 6-methyl-5-[3-(2,4,5-trimethylphenyl)propyl]pyrimidine-2,4-diamine Chemical compound C1=C(C)C(C)=CC(C)=C1CCCC1=C(C)N=C(N)N=C1N INGMERNHEAWFCU-UHFFFAOYSA-N 0.000 description 1
- YSUHRRLYFRXOEY-UHFFFAOYSA-N 6-methyl-5-[3-(4-methylphenyl)propyl]pyrimidine-2,4-diamine Chemical compound C1=CC(C)=CC=C1CCCC1=C(C)N=C(N)N=C1N YSUHRRLYFRXOEY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- LEQOFWKZHDPMEN-UHFFFAOYSA-N C(#N)C=CCCCC1=CC=CC2=CC=CC=C12 Chemical compound C(#N)C=CCCCC1=CC=CC2=CC=CC=C12 LEQOFWKZHDPMEN-UHFFFAOYSA-N 0.000 description 1
- PHTGQQSXWQOGCZ-UHFFFAOYSA-N C(CCCCCCCCCC)C=1C=C(OC=2C=NC=NC2)C=CC1 Chemical compound C(CCCCCCCCCC)C=1C=C(OC=2C=NC=NC2)C=CC1 PHTGQQSXWQOGCZ-UHFFFAOYSA-N 0.000 description 1
- BQXUPNKLZNSUMC-YUQWMIPFSA-N CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 Chemical compound CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 BQXUPNKLZNSUMC-YUQWMIPFSA-N 0.000 description 1
- 101100043727 Caenorhabditis elegans syx-2 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000005946 Cypermethrin Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 101100535673 Drosophila melanogaster Syn gene Proteins 0.000 description 1
- ICMAFTSLXCXHRK-UHFFFAOYSA-N Ethyl pentanoate Chemical compound CCCCC(=O)OCC ICMAFTSLXCXHRK-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- SSLMRMCNIMSAMJ-UHFFFAOYSA-N N#CC([Li])=COCC Chemical compound N#CC([Li])=COCC SSLMRMCNIMSAMJ-UHFFFAOYSA-N 0.000 description 1
- FFKZOUIEAHOBHW-UHFFFAOYSA-N N,4-dimethyl-N-nitrosobenzenesulfonamide Chemical compound O=NN(C)S(=O)(=O)C1=CC=C(C)C=C1 FFKZOUIEAHOBHW-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 208000037656 Respiratory Sounds Diseases 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- WGNIPMIDJBODIC-UHFFFAOYSA-N [4-(hydrazinylmethyl)phenyl]methylhydrazine Chemical compound NNCC1=CC=C(CNN)C=C1 WGNIPMIDJBODIC-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- VLLNJDMHDJRNFK-UHFFFAOYSA-N adamantan-1-ol Chemical compound C1C(C2)CC3CC2CC1(O)C3 VLLNJDMHDJRNFK-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- QBYJBZPUGVGKQQ-SJJAEHHWSA-N aldrin Chemical compound C1[C@H]2C=C[C@@H]1[C@H]1[C@@](C3(Cl)Cl)(Cl)C(Cl)=C(Cl)[C@@]3(Cl)[C@H]12 QBYJBZPUGVGKQQ-SJJAEHHWSA-N 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000005293 bicycloalkoxy group Chemical group 0.000 description 1
- OMFRMAHOUUJSGP-IRHGGOMRSA-N bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- OTJZCIYGRUNXTP-UHFFFAOYSA-N but-3-yn-1-ol Chemical compound OCCC#C OTJZCIYGRUNXTP-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- QOPVNWQGBQYBBP-UHFFFAOYSA-N chloroethyl chloroformate Chemical compound CC(Cl)OC(Cl)=O QOPVNWQGBQYBBP-UHFFFAOYSA-N 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940126208 compound 22 Drugs 0.000 description 1
- 229940125807 compound 37 Drugs 0.000 description 1
- 229940127573 compound 38 Drugs 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-N 0.000 description 1
- 229960001591 cyfluthrin Drugs 0.000 description 1
- 229960005424 cypermethrin Drugs 0.000 description 1
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 1
- 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000006353 environmental stress Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- GBIHOLCMZGAKNG-CGAIIQECSA-N flucythrinate Chemical compound O=C([C@@H](C(C)C)C=1C=CC(OC(F)F)=CC=1)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 GBIHOLCMZGAKNG-CGAIIQECSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- AILKHAQXUAOOFU-UHFFFAOYSA-N hexanenitrile Chemical compound CCCCCC#N AILKHAQXUAOOFU-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical class [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 235000011160 magnesium carbonates Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- XZJKVEKIQIHCIZ-UHFFFAOYSA-N pent-2-ynenitrile Chemical compound CCC#CC#N XZJKVEKIQIHCIZ-UHFFFAOYSA-N 0.000 description 1
- VMUWIDHKAIGONP-UHFFFAOYSA-N pent-4-ynenitrile Chemical compound C#CCCC#N VMUWIDHKAIGONP-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- LTXJLQINBYSQFU-UHFFFAOYSA-N pyrimidin-5-ol Chemical compound OC1=CN=CN=C1 LTXJLQINBYSQFU-UHFFFAOYSA-N 0.000 description 1
- MISVBCMQSJUHMH-UHFFFAOYSA-N pyrimidine-4,6-diamine Chemical class NC1=CC(N)=NC=N1 MISVBCMQSJUHMH-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 206010037833 rales Diseases 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- UGMFZXMMTLYNDY-UHFFFAOYSA-M sodium acetonitrile chloro(trimethyl)silane iodide Chemical compound [Na+].[I-].CC#N.C[Si](C)(C)Cl UGMFZXMMTLYNDY-UHFFFAOYSA-M 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 235000001508 sulfur Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- KMPQYAYAQWNLME-UHFFFAOYSA-N undecanal Chemical compound CCCCCCCCCCC=O KMPQYAYAQWNLME-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/20—N-Aryl derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US98508492A | 1992-12-02 | 1992-12-02 |
Publications (2)
Publication Number | Publication Date |
---|---|
AP9300595A0 AP9300595A0 (en) | 1994-01-31 |
AP503A true AP503A (en) | 1996-06-07 |
Family
ID=25531185
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
APAP/P/1993/000595A AP503A (en) | 1992-12-02 | 1993-12-01 | Insecticidal 5-substituted-2,4-diaminopyrimidine derivatives. |
Country Status (29)
Country | Link |
---|---|
US (3) | US5521192A (ru) |
EP (1) | EP0671881A4 (ru) |
JP (1) | JPH08502998A (ru) |
KR (1) | KR960700005A (ru) |
CN (1) | CN1096156A (ru) |
AP (1) | AP503A (ru) |
AU (1) | AU673222B2 (ru) |
BG (1) | BG99688A (ru) |
BR (1) | BR9307587A (ru) |
CA (1) | CA2150672A1 (ru) |
CO (1) | CO4180491A1 (ru) |
CZ (1) | CZ143295A3 (ru) |
FI (1) | FI952682A (ru) |
HR (1) | HRP931432A2 (ru) |
HU (1) | HUP9501597A2 (ru) |
LT (1) | LT3166B (ru) |
MA (1) | MA23044A1 (ru) |
MX (1) | MX9307471A (ru) |
NO (1) | NO952180L (ru) |
NZ (1) | NZ258722A (ru) |
OA (1) | OA10162A (ru) |
PL (1) | PL309259A1 (ru) |
RU (1) | RU95113597A (ru) |
SI (1) | SI9300624A (ru) |
SK (1) | SK73595A3 (ru) |
TN (1) | TNSN93133A1 (ru) |
TW (1) | TW311911B (ru) |
WO (1) | WO1994012032A1 (ru) |
ZA (1) | ZA938591B (ru) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6893815B1 (en) * | 1997-06-30 | 2005-05-17 | Isis Pharmaceuticals, Inc. | Nucleobase heterocyclic combinatorialization |
AU2001280445A1 (en) * | 2000-06-23 | 2002-01-08 | Vanderbilt University | Novel chain-breaking antioxidants |
BR0212186A (pt) | 2001-08-15 | 2004-10-05 | Du Pont | Composto, composição e método para controle de pragas invertebradas |
WO2004037791A1 (en) | 2002-10-21 | 2004-05-06 | Chiron Corporation | Inhibitors of glycogen synthase kinase 3 |
US20050171131A1 (en) * | 2003-09-26 | 2005-08-04 | Christi Kosogof | Diaminopyrimidine derivatives as growth hormone secrectgogue receptor (GHS-R) antagonists |
US20050070712A1 (en) * | 2003-09-26 | 2005-03-31 | Christi Kosogof | Pyrimidine derivatives as ghrelin receptor modulators |
DE102004003428A1 (de) * | 2004-01-23 | 2005-08-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue langwirksame Beta-2-Agonisten, und deren Verwendung als Arzneimittel |
JP2008532979A (ja) * | 2005-03-10 | 2008-08-21 | ビーエーエスエフ ソシエタス・ヨーロピア | 有害菌類を防除するための4−アミノピリミジン類の使用、新規の4−アミノピリミジン類、それらを調製する方法およびそれらを含む組成物 |
US9133212B1 (en) | 2005-06-15 | 2015-09-15 | Vanderbilt University | Inhibitors of hemeprotein-catalyzed lipid peroxidation |
US8367669B2 (en) * | 2005-06-15 | 2013-02-05 | Vanderbilt University | Inhibitors of hemeprotein-catalyzed lipid peroxidation |
AU2008236679B2 (en) * | 2007-04-03 | 2013-11-28 | Fmc Corporation | Substituted benzene fungicides |
CN101820879B (zh) * | 2007-10-08 | 2013-01-02 | 疟疾药物投资公司 | 具有柔性侧链的抗疟用化合物 |
US8110608B2 (en) | 2008-06-05 | 2012-02-07 | Ecolab Usa Inc. | Solid form sodium lauryl sulfate (SLS) pesticide composition |
US20120065067A1 (en) | 2010-09-14 | 2012-03-15 | The Regents Of The University Of California | Pamoic acid blocks ethylene signaling |
US8968757B2 (en) | 2010-10-12 | 2015-03-03 | Ecolab Usa Inc. | Highly wettable, water dispersible, granules including two pesticides |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4180578A (en) * | 1977-05-09 | 1979-12-25 | Ludwig Heumann, & Co. GmbH | 2,4-Diamino-5-(4'-methylthio)benzylpyrimidenes, compounds, compositions and method of use |
US4883798A (en) * | 1987-07-22 | 1989-11-28 | Egis Gyogyszergyar | Pharmaceutical compositions |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1229413A (ru) * | 1967-06-14 | 1971-04-21 | ||
JPS4829228A (ru) * | 1971-08-21 | 1973-04-18 | ||
GB1546937A (en) * | 1976-07-29 | 1979-05-31 | Beecham Group Ltd | 2,4-diaminopyrimidine derivatives |
GB2086386B (en) * | 1980-10-27 | 1984-01-18 | May & Baker Ltd | Pyrimidine derivatives |
US4438267A (en) * | 1980-11-11 | 1984-03-20 | Daluge Susan M | Monoheteroring compounds and their use |
PH20344A (en) * | 1981-01-29 | 1986-12-04 | Sankyo Co | Aminopyrimidine derivatives, processes for their preparation, and fungicidal, insecticidal and acaricidal compositions containing them |
AU589409B2 (en) * | 1985-03-14 | 1989-10-12 | Sankyo Company Limited | Phenoxyalkylaminopyrimidine derivatives, their preparation and insecticidal and acaricidal compositions containing them |
US4783468A (en) * | 1986-04-30 | 1988-11-08 | Ciba-Geigy Corporation | Insecticidal 5-pyrimidine carbonitriles |
US4895849A (en) * | 1986-10-08 | 1990-01-23 | Ube Industries, Ltd. | Aralkylaminopyrimidine compounds which are useful as for producing thereof and insecticides |
JPH0720943B2 (ja) * | 1988-08-19 | 1995-03-08 | 宇部興産株式会社 | アミノピリミジン誘導体、その製法及び殺虫・殺菌剤 |
-
1992
- 1992-11-18 RU RU95113597/04A patent/RU95113597A/ru unknown
-
1993
- 1993-11-17 ZA ZA938591A patent/ZA938591B/xx unknown
- 1993-11-18 CZ CZ951432A patent/CZ143295A3/cs unknown
- 1993-11-18 KR KR1019950702250A patent/KR960700005A/ko not_active Application Discontinuation
- 1993-11-18 EP EP94902306A patent/EP0671881A4/en not_active Withdrawn
- 1993-11-18 JP JP6513259A patent/JPH08502998A/ja active Pending
- 1993-11-18 BR BR9307587-1A patent/BR9307587A/pt not_active Application Discontinuation
- 1993-11-18 AU AU56716/94A patent/AU673222B2/en not_active Ceased
- 1993-11-18 CA CA002150672A patent/CA2150672A1/en not_active Abandoned
- 1993-11-18 HU HU9501597A patent/HUP9501597A2/hu unknown
- 1993-11-18 NZ NZ258722A patent/NZ258722A/en unknown
- 1993-11-18 SK SK735-95A patent/SK73595A3/sk unknown
- 1993-11-18 PL PL93309259A patent/PL309259A1/xx unknown
- 1993-11-18 WO PCT/US1993/011240 patent/WO1994012032A1/en not_active Application Discontinuation
- 1993-11-24 HR HR931432A patent/HRP931432A2/hr not_active Application Discontinuation
- 1993-11-26 CO CO93420258A patent/CO4180491A1/es unknown
- 1993-11-29 MX MX9307471A patent/MX9307471A/es unknown
- 1993-11-30 MA MA23352A patent/MA23044A1/fr unknown
- 1993-12-01 AP APAP/P/1993/000595A patent/AP503A/en active
- 1993-12-01 LT LTIP1510A patent/LT3166B/lt not_active IP Right Cessation
- 1993-12-02 CN CN93120401A patent/CN1096156A/zh active Pending
- 1993-12-02 SI SI9300624A patent/SI9300624A/sl unknown
- 1993-12-02 TW TW082110271A patent/TW311911B/zh active
- 1993-12-02 TN TNTNSN93133A patent/TNSN93133A1/fr unknown
-
1994
- 1994-05-03 US US08/237,481 patent/US5521192A/en not_active Expired - Fee Related
-
1995
- 1995-05-22 US US08/446,354 patent/US5587379A/en not_active Expired - Fee Related
- 1995-05-31 BG BG99688A patent/BG99688A/xx unknown
- 1995-06-01 FI FI952682A patent/FI952682A/fi unknown
- 1995-06-01 NO NO952180A patent/NO952180L/no unknown
- 1995-06-02 OA OA60670A patent/OA10162A/en unknown
- 1995-11-08 US US08/555,249 patent/US5627189A/en not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4180578A (en) * | 1977-05-09 | 1979-12-25 | Ludwig Heumann, & Co. GmbH | 2,4-Diamino-5-(4'-methylthio)benzylpyrimidenes, compounds, compositions and method of use |
US4883798A (en) * | 1987-07-22 | 1989-11-28 | Egis Gyogyszergyar | Pharmaceutical compositions |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
AP503A (en) | Insecticidal 5-substituted-2,4-diaminopyrimidine derivatives. | |
AP506A (en) | Insecticidal substituted-2,4-diaminoquinazolines. | |
US6153619A (en) | Aryl-substituted pyrimidines as insecticidal and acaricidal agents | |
LT3663B (en) | Pyridine derivatives, process for their production, herbicidal method and composition | |
JPH02286666A (ja) | 有害生物防除組成物 | |
LV10613B (en) | Method for preparation of 2-anilino-pyrimidine derivatives, 2-anilino-pyrimidine derivatives, remedies and method for the control of undesired insects, process for preparing of agrochemical remedy | |
EP0238711A1 (en) | Thiadiazabicyclononane derivatives, processes for their production and herbizidal compositions | |
US5532367A (en) | Insecticidal pteridines and 8-deazapteridines | |
US5622954A (en) | 5[W(substituted aryl)alkenylene and alkynylene]-2,4-diaminopyrimidines as pesticides | |
US5164396A (en) | Barbituric acid derivatives having insecticidal activity | |
JPH11503115A (ja) | シクロヘキシルアミノおよびシクロヘキシルアルコキシ窒素複素環化合物、それらの製法および殺虫剤および殺菌剤としてのそれらの使用 | |
JPH06157469A (ja) | ピラゾールカルボニルウレア誘導体、その製法及び有害生物防除剤 | |
US5478799A (en) | N-sulfonyl carboxylic amide derivative including an N-containing 6-membered aromatic ring, or salt of the same, method for producing the same, and biocide | |
US5565451A (en) | 1-substituted-2, 4-diamino-6, 6-dialkyl-1, 6-dihydro-1, 3, 5-triazines as insecticides | |
JP2707239B2 (ja) | シアノアルキルーヘテロ環式化合物及び殺虫剤 | |
US5696259A (en) | 2,4-diamino-5-iodopyrimidines useful as pesticide intermediates | |
CA1103675A (en) | 2-substituted-n-(3-substituted phenyl)-oxazolidine-3- carbothioamides | |
JPH0789941A (ja) | フェニルグアニジン誘導体および除草剤 | |
JPH06316572A (ja) | 新規ヘテロ環式化合物及び殺虫剤 | |
JPS61268694A (ja) | 含フツ素有機リン酸エステル誘導体およびそれを有効成分とする殺虫、殺ダニ剤 | |
JPH05504946A (ja) | 殺真菌剤組成物、それらの製造および用途 | |
JPS61267561A (ja) | 殺虫性ニトロメチレン誘導体 | |
JPH09110839A (ja) | ピリミジン又はトリアジン誘導体及びこれらを有効成分として含有する除草剤 |