UA81012C2 - Avermectin monosaccharide derivatives - Google Patents

Info

Publication number

UA81012C2

UA81012C2 UAA200508413A UA2005008413A UA81012C2 UA 81012 C2 UA81012 C2 UA 81012C2 UA A200508413 A UAA200508413 A UA A200508413A UA 2005008413 A UA2005008413 A UA 2005008413A UA 81012 C2 UA81012 C2 UA 81012C2

Authority

UA

Ukraine

Prior art keywords

formula

compounds

compound

configuration

aryl

Prior art date

2003-01-31

Links

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• Global Dossier
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• -1 Avermectin monosaccharide derivatives Chemical class 0.000 title claims description 95
• 239000005660 Abamectin Substances 0.000 title claims description 9
• 150000001875 compounds Chemical class 0.000 claims abstract description 552
• 239000000203 mixture Substances 0.000 claims abstract description 84
• 229910052799 carbon Inorganic materials 0.000 claims description 150
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 58
• 125000003118 aryl group Chemical group 0.000 claims description 45
• 150000003839 salts Chemical class 0.000 claims description 32
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 29
• 125000000623 heterocyclic group Chemical group 0.000 claims description 27
• 125000001424 substituent group Chemical group 0.000 claims description 26
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 22
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
• 229910052736 halogen Inorganic materials 0.000 claims description 19
• 125000000217 alkyl group Chemical group 0.000 claims description 18
• 150000002367 halogens Chemical class 0.000 claims description 17
• 125000002947 alkylene group Chemical group 0.000 claims description 16
• 238000006467 substitution reaction Methods 0.000 claims description 16
• 229910052739 hydrogen Inorganic materials 0.000 claims description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• 125000004104 aryloxy group Chemical group 0.000 claims description 9
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 9
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 9
• 125000001072 heteroaryl group Chemical group 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 5
• 125000004414 alkyl thio group Chemical group 0.000 claims description 4
• 125000005110 aryl thio group Chemical group 0.000 claims description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
• 125000004450 alkenylene group Chemical group 0.000 claims description 3
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
• 150000002771 monosaccharide derivatives Chemical class 0.000 claims description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 2
• 125000004468 heterocyclylthio group Chemical group 0.000 claims description 2
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
• 125000005843 halogen group Chemical group 0.000 claims 2
• 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims 1
• 238000012876 topography Methods 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 101
• 241000607479 Yersinia pestis Species 0.000 abstract description 20
• 238000002360 preparation method Methods 0.000 abstract description 8
• 230000000361 pesticidal effect Effects 0.000 abstract description 3
• 239000000543 intermediate Substances 0.000 abstract description 2
• 150000001721 carbon Chemical class 0.000 description 147
• 239000002904 solvent Substances 0.000 description 74
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
• 238000006243 chemical reaction Methods 0.000 description 66
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 64
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 63
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
• 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 49
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 48
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
• 239000002585 base Substances 0.000 description 48
• 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 48
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 39
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 32
• 241000196324 Embryophyta Species 0.000 description 30
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
• 150000002772 monosaccharides Chemical class 0.000 description 25
• 241000238631 Hexapoda Species 0.000 description 23
• 239000004480 active ingredient Substances 0.000 description 20
• 238000009835 boiling Methods 0.000 description 19
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 18
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
• 125000004432 carbon atom Chemical group C* 0.000 description 17
• 150000002170 ethers Chemical class 0.000 description 17
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
• 230000000694 effects Effects 0.000 description 16
• 230000003993 interaction Effects 0.000 description 16
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• 125000001931 aliphatic group Chemical group 0.000 description 15
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 14
• 150000001412 amines Chemical class 0.000 description 14
• 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 14
• 150000008282 halocarbons Chemical class 0.000 description 14
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 13
• 150000001408 amides Chemical class 0.000 description 13
• 238000004587 chromatography analysis Methods 0.000 description 13
• 229930195733 hydrocarbon Natural products 0.000 description 13
• 229910000027 potassium carbonate Inorganic materials 0.000 description 13
• 150000002825 nitriles Chemical class 0.000 description 12
• YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 12
• 229920006395 saturated elastomer Polymers 0.000 description 11
• 239000007787 solid Substances 0.000 description 11
• 239000000126 substance Substances 0.000 description 11
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
• 239000002202 Polyethylene glycol Substances 0.000 description 10
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
• 239000002253 acid Substances 0.000 description 10
• 239000000460 chlorine Substances 0.000 description 10
• 229910052801 chlorine Inorganic materials 0.000 description 10
• 235000008504 concentrate Nutrition 0.000 description 10
• 239000012141 concentrate Substances 0.000 description 10
• 150000002148 esters Chemical class 0.000 description 10
• 150000007530 organic bases Chemical class 0.000 description 10
• 229920001223 polyethylene glycol Polymers 0.000 description 10
• 239000012279 sodium borohydride Substances 0.000 description 10
• 229910000033 sodium borohydride Inorganic materials 0.000 description 10
• 239000000243 solution Substances 0.000 description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
• 229910052794 bromium Inorganic materials 0.000 description 9
• 230000006378 damage Effects 0.000 description 9
• 235000014113 dietary fatty acids Nutrition 0.000 description 9
• 239000000194 fatty acid Substances 0.000 description 9
• 229930195729 fatty acid Natural products 0.000 description 9
• 229910052731 fluorine Inorganic materials 0.000 description 9
• 239000011737 fluorine Substances 0.000 description 9
• 239000012074 organic phase Substances 0.000 description 9
• 239000012071 phase Substances 0.000 description 9
• 230000009467 reduction Effects 0.000 description 9
• 239000000741 silica gel Substances 0.000 description 9
• 229910002027 silica gel Inorganic materials 0.000 description 9
• 229910052938 sodium sulfate Inorganic materials 0.000 description 9
• 235000011152 sodium sulphate Nutrition 0.000 description 9
• 239000004094 surface-active agent Substances 0.000 description 9
• 241001465754 Metazoa Species 0.000 description 8
• 239000000654 additive Substances 0.000 description 8
• 125000004429 atom Chemical group 0.000 description 8
• 239000003638 chemical reducing agent Substances 0.000 description 8
• 239000000839 emulsion Substances 0.000 description 8
• 235000019441 ethanol Nutrition 0.000 description 8
• 239000008187 granular material Substances 0.000 description 8
• 239000007788 liquid Substances 0.000 description 8
• 239000007858 starting material Substances 0.000 description 8
• 239000007864 aqueous solution Substances 0.000 description 7
• 229940079593 drug Drugs 0.000 description 7
• 239000003814 drug Substances 0.000 description 7
• 238000004128 high performance liquid chromatography Methods 0.000 description 7
• 229910052740 iodine Inorganic materials 0.000 description 7
• 239000000463 material Substances 0.000 description 7
• IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 7
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 7
• IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 description 6
• 239000005995 Aluminium silicate Substances 0.000 description 6
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
• 240000001307 Myosotis scorpioides Species 0.000 description 6
• 150000001298 alcohols Chemical class 0.000 description 6
• 235000012211 aluminium silicate Nutrition 0.000 description 6
• 239000011248 coating agent Substances 0.000 description 6
• 238000000576 coating method Methods 0.000 description 6
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
• 235000013399 edible fruits Nutrition 0.000 description 6
• 125000001153 fluoro group Chemical group F* 0.000 description 6
• 125000001188 haloalkyl group Chemical group 0.000 description 6
• NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 6
• 238000002156 mixing Methods 0.000 description 6
• 241000244206 Nematoda Species 0.000 description 5
• 150000007513 acids Chemical class 0.000 description 5
• 239000002671 adjuvant Substances 0.000 description 5
• 229910052783 alkali metal Inorganic materials 0.000 description 5
• 150000001735 carboxylic acids Chemical class 0.000 description 5
• 239000004359 castor oil Substances 0.000 description 5
• 235000019438 castor oil Nutrition 0.000 description 5
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
• 150000004665 fatty acids Chemical class 0.000 description 5
• 229910052700 potassium Inorganic materials 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• 239000000047 product Substances 0.000 description 5
• 239000012266 salt solution Substances 0.000 description 5
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• 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 4
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• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
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• 235000019864 coconut oil Nutrition 0.000 description 4
• 238000011161 development Methods 0.000 description 4
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• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
• 239000008096 xylene Substances 0.000 description 4
• VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 4
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• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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• RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical class C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 description 3
• CJJOSEISRRTUQB-UHFFFAOYSA-N azinphos-methyl Chemical group C1=CC=C2C(=O)N(CSP(=S)(OC)OC)N=NC2=C1 CJJOSEISRRTUQB-UHFFFAOYSA-N 0.000 description 3
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• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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• 150000003672 ureas Chemical class 0.000 description 1
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• 229910052720 vanadium Inorganic materials 0.000 description 1
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• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
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• WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
• 239000008434 yi-zhi Substances 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1