OA10143A - 13-Substituted milbemycin derivatives their preparation and use - Google Patents

13-Substituted milbemycin derivatives their preparation and use Download PDF

Info

Publication number: OA10143A
Authority: OA; OAPI
Prior art keywords: group; carbon atoms; milbemycin; substituents; doublet
Prior art date: 1994-04-01

Application number

OA60633A

Other languages

English (en)

Inventor

Takeshiba Hideo

Sato Kazuo

Yanai Toshiaki

Yokoi Shinji

Ichinose Reiji

Tanizawa Kinji

Original Assignee

Sankyo Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1994-04-01

Filing date

1995-03-31

Publication date

1996-12-18

1995-03-31 Application filed by Sankyo Co filed Critical Sankyo Co

1996-12-18 Publication of OA10143A publication Critical patent/OA10143A/en

Links

FXWHFKOXMBTCMP-WMEDONTMSA-N milbemycin Natural products COC1C2OCC3=C/C=C/C(C)CC(=CCC4CC(CC5(O4)OC(C)C(C)C(OC(=O)C(C)CC(C)C)C5O)OC(=O)C(C=C1C)C23O)C FXWHFKOXMBTCMP-WMEDONTMSA-N 0.000 title claims abstract description 40
238000002360 preparation method Methods 0.000 title description 11
-1 N-substituted-aminophenyl Chemical group 0.000 claims abstract description 154
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 78
125000000217 alkyl group Chemical group 0.000 claims abstract description 34
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 33
230000000895 acaricidal effect Effects 0.000 claims abstract description 18
230000000507 anthelmentic effect Effects 0.000 claims abstract description 15
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 15
150000001875 compounds Chemical class 0.000 claims description 341
125000004432 carbon atom Chemical group C* 0.000 claims description 196
125000001424 substituent group Chemical group 0.000 claims description 136
239000000203 mixture Substances 0.000 claims description 74
125000004429 atom Chemical group 0.000 claims description 53
VOZIAWLUULBIPN-LRBNAKOISA-N milbemycin A4 Chemical compound C1C[C@H](C)[C@@H](CC)O[C@@]21O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 VOZIAWLUULBIPN-LRBNAKOISA-N 0.000 claims description 46
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
238000000034 method Methods 0.000 claims description 37
125000003277 amino group Chemical group 0.000 claims description 33
229910052757 nitrogen Inorganic materials 0.000 claims description 30
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 29
229910052799 carbon Inorganic materials 0.000 claims description 29
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 27
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 25
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 25
125000002252 acyl group Chemical group 0.000 claims description 24
125000000623 heterocyclic group Chemical group 0.000 claims description 24
229920006395 saturated elastomer Polymers 0.000 claims description 21
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
125000003118 aryl group Chemical group 0.000 claims description 17
125000001589 carboacyl group Chemical group 0.000 claims description 17
229910052801 chlorine Inorganic materials 0.000 claims description 17
229910052731 fluorine Inorganic materials 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 15
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical compound O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[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 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 claims description 13
241000238631 Hexapoda Species 0.000 claims description 12
125000005129 aryl carbonyl group Chemical group 0.000 claims description 12
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
229910052794 bromium Inorganic materials 0.000 claims description 12
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 12
125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
125000005236 alkanoylamino group Chemical group 0.000 claims description 11
125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
244000045947 parasite Species 0.000 claims description 11
125000006413 ring segment Chemical group 0.000 claims description 11
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 10
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 10
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 10
230000000749 insecticidal effect Effects 0.000 claims description 10
125000004414 alkyl thio group Chemical group 0.000 claims description 9
GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 claims description 9
125000002541 furyl group Chemical group 0.000 claims description 9
125000001544 thienyl group Chemical group 0.000 claims description 9
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 8
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 8
239000003085 diluting agent Substances 0.000 claims description 8
125000004076 pyridyl group Chemical group 0.000 claims description 8
230000001850 reproductive effect Effects 0.000 claims description 8
125000000335 thiazolyl group Chemical group 0.000 claims description 8
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 7
125000002971 oxazolyl group Chemical group 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
125000001153 fluoro group Chemical group F* 0.000 claims description 6
125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 6
125000004443 haloalkoxycarbonylamino group Chemical group 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
241000500891 Insecta Species 0.000 claims description 4
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
244000000013 helminth Species 0.000 claims description 3
125000006626 methoxycarbonylamino group Chemical group 0.000 claims description 3
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
125000000676 alkoxyimino group Chemical group 0.000 claims 1
UWHWNFVVODLFIQ-UHFFFAOYSA-N methyl pyrrolidine-1-carboxylate Chemical compound COC(=O)N1CCCC1 UWHWNFVVODLFIQ-UHFFFAOYSA-N 0.000 claims 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract description 12
239000002917 insecticide Substances 0.000 abstract description 3
229910052739 hydrogen Inorganic materials 0.000 abstract description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
239000001257 hydrogen Substances 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 126
238000001228 spectrum Methods 0.000 description 119
238000006243 chemical reaction Methods 0.000 description 105
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 57
239000002253 acid Substances 0.000 description 54
239000002904 solvent Substances 0.000 description 44
229940093499 ethyl acetate Drugs 0.000 description 42
235000019439 ethyl acetate Nutrition 0.000 description 42
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 34
238000001819 mass spectrum Methods 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
239000000243 solution Substances 0.000 description 30
239000000460 chlorine Substances 0.000 description 29
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
239000007864 aqueous solution Substances 0.000 description 26
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
235000002639 sodium chloride Nutrition 0.000 description 24
239000000284 extract Substances 0.000 description 23
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
239000007858 starting material Substances 0.000 description 21
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
239000011541 reaction mixture Substances 0.000 description 20
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
229960002668 sodium chloride Drugs 0.000 description 17
239000011780 sodium chloride Substances 0.000 description 17
230000000694 effects Effects 0.000 description 16
229960001866 silicon dioxide Drugs 0.000 description 16
239000000741 silica gel Substances 0.000 description 15
229910002027 silica gel Inorganic materials 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
238000004440 column chromatography Methods 0.000 description 13
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 12
239000011737 fluorine Substances 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 11
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 11
239000002585 base Substances 0.000 description 11
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
239000003153 chemical reaction reagent Substances 0.000 description 11
238000001816 cooling Methods 0.000 description 11
150000002148 esters Chemical class 0.000 description 11
150000004820 halides Chemical class 0.000 description 11
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
239000004094 surface-active agent Substances 0.000 description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
238000009472 formulation Methods 0.000 description 9
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 9
239000012279 sodium borohydride Substances 0.000 description 9
229910000033 sodium borohydride Inorganic materials 0.000 description 9
239000000126 substance Substances 0.000 description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
241000196324 Embryophyta Species 0.000 description 8
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
238000002143 fast-atom bombardment mass spectrum Methods 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
235000011054 acetic acid Nutrition 0.000 description 7
229960000583 acetic acid Drugs 0.000 description 7
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 7
239000003638 chemical reducing agent Substances 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 7
229940124024 weight reducing agent Drugs 0.000 description 7
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
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 6
241001465754 Metazoa Species 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
241000534944 Thia Species 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
150000001732 carboxylic acid derivatives Chemical group 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
239000000463 material Substances 0.000 description 6
230000001473 noxious effect Effects 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
229960001407 sodium bicarbonate Drugs 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
YOJHBFHEOQUUAR-UHFFFAOYSA-N 1-(4-nitrophenyl)ethane-1,2-diol Chemical compound OCC(O)C1=CC=C([N+]([O-])=O)C=C1 YOJHBFHEOQUUAR-UHFFFAOYSA-N 0.000 description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
239000012043 crude product Substances 0.000 description 5
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 5
150000002170 ethers Chemical class 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
229910052740 iodine Inorganic materials 0.000 description 5
239000011630 iodine Substances 0.000 description 5
239000003120 macrolide antibiotic agent Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
238000000746 purification Methods 0.000 description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
239000005660 Abamectin Substances 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
125000001980 alanyl group Chemical group 0.000 description 4
229910052786 argon Inorganic materials 0.000 description 4
239000000969 carrier Substances 0.000 description 4
GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 4
235000014113 dietary fatty acids Nutrition 0.000 description 4
ZFCXKZCKJZFZGR-UHFFFAOYSA-N ethyl 2-(4-nitrophenyl)-2-oxoacetate Chemical compound CCOC(=O)C(=O)C1=CC=C([N+]([O-])=O)C=C1 ZFCXKZCKJZFZGR-UHFFFAOYSA-N 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
229930195729 fatty acid Natural products 0.000 description 4
125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens Chemical class 0.000 description 4
239000007788 liquid Substances 0.000 description 4
230000003071 parasitic effect Effects 0.000 description 4
235000019260 propionic acid Nutrition 0.000 description 4
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
NJGXCDVXXRSHEB-UHFFFAOYSA-N 1-(2-chlorophenyl)-2-hydroxyethanone Chemical compound OCC(=O)C1=CC=CC=C1Cl NJGXCDVXXRSHEB-UHFFFAOYSA-N 0.000 description 3
ABFPKTQEQNICFT-UHFFFAOYSA-M 2-chloro-1-methylpyridin-1-ium;iodide Chemical compound [I-].C[N+]1=CC=CC=C1Cl ABFPKTQEQNICFT-UHFFFAOYSA-M 0.000 description 3
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
RREPYIWLDJQENS-UHFFFAOYSA-N 4-nitrophenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=C([N+]([O-])=O)C=C1 RREPYIWLDJQENS-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
206010049119 Emotional distress Diseases 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
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KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
239000004698 Polyethylene Substances 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
239000000654 additive Substances 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
125000004744 butyloxycarbonyl group Chemical group 0.000 description 3
239000007810 chemical reaction solvent Substances 0.000 description 3
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000012024 dehydrating agents‎ Substances 0.000 description 3
230000009429 distress Effects 0.000 description 3
239000004495 emulsifiable concentrate Substances 0.000 description 3
150000004665 fatty acids Chemical class 0.000 description 3
239000000499 gel Substances 0.000 description 3
150000008282 halocarbons Chemical class 0.000 description 3
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241001494479 Pecora Species 0.000 description 1
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231100000674 Phytotoxicity Toxicity 0.000 description 1
235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
235000011613 Pinus brutia Nutrition 0.000 description 1
241000018646 Pinus brutia Species 0.000 description 1
241000500439 Plutella Species 0.000 description 1
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241001097374 Pselliopus cinctus Species 0.000 description 1
241000596535 Pseudococcus comstocki Species 0.000 description 1
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239000004113 Sepiolite Substances 0.000 description 1
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241000254154 Sitophilus zeamais Species 0.000 description 1
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229920001938 Vegetable gum Polymers 0.000 description 1
101710097421 WD repeat and HMG-box DNA-binding protein 1 Chemical group 0.000 description 1
102100029469 WD repeat and HMG-box DNA-binding protein 1 Human genes 0.000 description 1
241000244002 Wuchereria Species 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
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239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
ZUQAPLKKNAQJAU-UHFFFAOYSA-N acetylenediol Chemical class OC#CO ZUQAPLKKNAQJAU-UHFFFAOYSA-N 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
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239000003513 alkali Substances 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
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235000012211 aluminium silicate Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
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239000002775 capsule Substances 0.000 description 1
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150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000004927 clay Substances 0.000 description 1
AVWLPUQJODERGA-UHFFFAOYSA-L cobalt(2+);diiodide Chemical compound [Co+2].[I-].[I-] AVWLPUQJODERGA-UHFFFAOYSA-L 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
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239000002385 cottonseed oil Substances 0.000 description 1
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125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
244000078703 ectoparasite Species 0.000 description 1
230000001984 ectoparasiticidal effect Effects 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
235000013601 eggs Nutrition 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
BSMODAKHHXOWDP-UHFFFAOYSA-N ethyl 2-methoxyimino-2-phenylacetate Chemical compound CCOC(=O)C(=NOC)C1=CC=CC=C1 BSMODAKHHXOWDP-UHFFFAOYSA-N 0.000 description 1
RQDSWUCVBZVOSH-UHFFFAOYSA-N ethyl 2-oxo-2-pyridin-2-ylacetate Chemical compound CCOC(=O)C(=O)C1=CC=CC=N1 RQDSWUCVBZVOSH-UHFFFAOYSA-N 0.000 description 1
NGRXSVFCLHVGKU-UHFFFAOYSA-N ethyl 3-(4-nitrophenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C([N+]([O-])=O)C=C1 NGRXSVFCLHVGKU-UHFFFAOYSA-N 0.000 description 1
235000019387 fatty acid methyl ester Nutrition 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
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239000003337 fertilizer Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
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150000002334 glycols Chemical class 0.000 description 1
238000000227 grinding Methods 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000002484 inorganic compounds Chemical class 0.000 description 1
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238000007689 inspection Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000008040 ionic compounds Chemical class 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
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 1
150000002576 ketones Chemical class 0.000 description 1
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239000008101 lactose Substances 0.000 description 1
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210000003097 mucus Anatomy 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000001069 nematicidal effect Effects 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
BFSQJYRFLQUZKX-UHFFFAOYSA-L nickel(ii) iodide Chemical compound I[Ni]I BFSQJYRFLQUZKX-UHFFFAOYSA-L 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
125000005646 oximino group Chemical group 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
230000007096 poisonous effect Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001983 poloxamer Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
244000144977 poultry Species 0.000 description 1
125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-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
229940090181 propyl acetate Drugs 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
239000008262 pumice Substances 0.000 description 1
BJDYCCHRZIFCGN-UHFFFAOYSA-N pyridin-1-ium;iodide Chemical compound I.C1=CC=NC=C1 BJDYCCHRZIFCGN-UHFFFAOYSA-N 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
239000004576 sand Substances 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229940074404 sodium succinate Drugs 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000000758 substrate Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000000375 suspending agent Substances 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
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
238000000825 ultraviolet detection Methods 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Landscapes

Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
Agronomy & Crop Science (AREA)
Dentistry (AREA)
Molecular Biology (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Genetics & Genomics (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

OA60633A 1994-04-01 1995-03-31 13-Substituted milbemycin derivatives their preparation and use OA10143A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP6480394		1994-04-01
JP28338294		1994-11-17
JP937795		1995-01-25

Publications (1)

Publication Number	Publication Date
OA10143A true OA10143A (en)	1996-12-18

Family

ID=27278452

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA60633A OA10143A (en)	1994-04-01	1995-03-31	13-Substituted milbemycin derivatives their preparation and use

Country Status (23)

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US (1)	US5614470A (pl)
EP (1)	EP0675133B1 (pl)
KR (1)	KR100221823B1 (pl)
CN (1)	CN1058011C (pl)
AP (1)	AP563A (pl)
AT (1)	ATE188705T1 (pl)
AU (1)	AU682439B2 (pl)
CA (1)	CA2146047C (pl)
DE (1)	DE69514398T2 (pl)
DK (1)	DK0675133T3 (pl)
EG (1)	EG21121A (pl)
ES (1)	ES2143004T3 (pl)
GR (1)	GR3032847T3 (pl)
HU (1)	HU215078B (pl)
IL (1)	IL113195A (pl)
MX (1)	MX9501622A (pl)
NZ (1)	NZ270850A (pl)
OA (1)	OA10143A (pl)
PL (1)	PL181779B1 (pl)
RU (1)	RU2109744C1 (pl)
TR (1)	TR28331A (pl)
TW (1)	TW305745B (pl)
ZA (1)	ZA952649B (pl)

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JPH08223902A (ja) *	1995-02-14	1996-08-30	Mitsubishi Heavy Ind Ltd	ディスク型ｍｈｄ発電機
PT765879E (pt) *	1995-09-29	2001-05-31	Sankyo Co	Derivados 13-substituidos de milbemicina-5-oxima sua preparacao e utilizacao contra insectos e outras pragas
NZ522247A (en)	2000-04-27	2004-07-30	Sankyo Lifetech Company Ltd	13-substituted milbemycin derivatives, their preparation and their use against insects and other pests
RU2251842C1 (ru) *	2003-10-29	2005-05-20	Всероссийский научно-исследовательский институт ветеринарной санитарии, гигиены и экологии	Инсектицидный состав для борьбы с личинками оводов эга-1
RU2251267C1 (ru) *	2003-10-29	2005-05-10	Всероссийский научно-исследовательский институт ветеринарной санитарии, гигиены и экологии	Инсектицидный состав для борьбы с личинками оводов эга-2
NZ598569A (en) *	2005-11-14	2013-04-26	Rhodia	Surfactant is sulfonate in an agricultural adjuvant compositions, pesticide compositions, and methods for using such compositions
EP1849363A1 (en) *	2006-03-09	2007-10-31	Cheminova A/S	Synergistic combination of glutamate- and GABA-gated chloride agonist pesticide and at least one of Vitamin E or Niacin
DE102007045922A1 (de)	2007-09-26	2009-04-02	Bayer Cropscience Ag	Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften
EP2127522A1 (de)	2008-05-29	2009-12-02	Bayer CropScience AG	Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften
EP2227951A1 (de)	2009-01-23	2010-09-15	Bayer CropScience AG	Verwendung von Enaminocarbonylverbindungen zur Bekämpfung von durch Insekten übertragenen Viren
EP2382865A1 (de)	2010-04-28	2011-11-02	Bayer CropScience AG	Synergistische Wirkstoffkombinationen
CN102165955A (zh) *	2011-03-11	2011-08-31	青岛海利尔药业有限公司	一种含有生物农药与双酰肼类农药的高效环保杀虫组合物
CN111217828B (zh) *	2018-11-26	2022-11-25	浙江海正药业股份有限公司	一种乐平霉素的制备方法及其中间体
EP3959207A1 (en)	2019-04-26	2022-03-02	Celgene Corporation	Heterocyclic compounds and their use for treatment of helminthic infections and diseases
WO2022087326A1 (en) *	2020-10-23	2022-04-28	Celgene Corporation	Heterocyclic compounds and their use for treatment of helminthic infections and diseases

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JPS5632481A (en) *	1979-08-23	1981-04-01	Sankyo Co Ltd	Antibiotic b-41d, its preparation, and acaricide and anthelminthic agent and repellent containing the same as active constituent
JPS59108785A (ja) *	1982-11-25	1984-06-23	Sankyo Co Ltd	ミルベマイシン類の５−オキシム誘導体
JPS6289685A (ja) *	1985-05-31	1987-04-24	Sankyo Co Ltd	１３−ハロゲンミルベマイシン誘導体
RU2024527C1 (ru) *	1986-03-25	1994-12-15	Санкио Компани Лимитед	Способ получения макролидных соединений
EP0246793A3 (en) *	1986-05-19	1988-06-01	AT&T Corp.	High-power, fundamental transverse mode laser
GB8811037D0 (en) *	1988-05-10	1988-06-15	Glaxo Group Ltd	Chemical compounds
AU613521B2 (en) *	1988-09-02	1991-08-01	Sankyo Company Limited	13-substituted milbemycin derivatives, their preparation and use
US5428034A (en) *	1988-09-02	1995-06-27	Sankyo Co., Ltd.	Milbemycin derivatives, their preparation and their use
JPH085894B2 (ja) *	1990-03-01	1996-01-24	三共株式会社	ミルベマイシンエーテル誘導体
JP2622197B2 (ja) *	1990-03-01	1997-06-18	三共株式会社	１３−エーテル置換ミルベマイシン誘導体
KR0171426B1 (ko) *	1991-12-18	1999-02-01	가와무라 요시부미	13-(치환 티오) 아세톡시밀베마이신 유도체, 그의 제조방법 및 농화학적 용도

1995
- 1995-03-29 US US08/412,687 patent/US5614470A/en not_active Expired - Lifetime
- 1995-03-30 AP APAP/P/1995/000727A patent/AP563A/en active
- 1995-03-30 IL IL11319595A patent/IL113195A/en not_active IP Right Cessation
- 1995-03-30 ZA ZA952649A patent/ZA952649B/xx unknown
- 1995-03-31 TR TR00358/95A patent/TR28331A/xx unknown
- 1995-03-31 NZ NZ270850A patent/NZ270850A/en not_active IP Right Cessation
- 1995-03-31 EP EP95302165A patent/EP0675133B1/en not_active Expired - Lifetime
- 1995-03-31 TW TW084103120A patent/TW305745B/zh not_active IP Right Cessation
- 1995-03-31 OA OA60633A patent/OA10143A/en unknown
- 1995-03-31 AT AT95302165T patent/ATE188705T1/de not_active IP Right Cessation
- 1995-03-31 CN CN95105102A patent/CN1058011C/zh not_active Expired - Lifetime
- 1995-03-31 PL PL95307949A patent/PL181779B1/pl not_active IP Right Cessation
- 1995-03-31 DE DE69514398T patent/DE69514398T2/de not_active Expired - Fee Related
- 1995-03-31 AU AU16203/95A patent/AU682439B2/en not_active Ceased
- 1995-03-31 HU HU9500945A patent/HU215078B/hu not_active IP Right Cessation
- 1995-03-31 DK DK95302165T patent/DK0675133T3/da active
- 1995-03-31 CA CA002146047A patent/CA2146047C/en not_active Expired - Fee Related
- 1995-03-31 ES ES95302165T patent/ES2143004T3/es not_active Expired - Lifetime
- 1995-03-31 RU RU95104884/04A patent/RU2109744C1/ru active
- 1995-03-31 MX MX9501622A patent/MX9501622A/es unknown
- 1995-04-01 KR KR1019950007646A patent/KR100221823B1/ko not_active Expired - Lifetime
- 1995-04-01 EG EG26295A patent/EG21121A/xx active
2000
- 2000-03-03 GR GR20000400539T patent/GR3032847T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
TR28331A (tr)	1996-05-06
CA2146047C (en)	2005-07-12
EP0675133A1 (en)	1995-10-04
HUT75949A (en)	1997-05-28
IL113195A (en)	1998-08-16
DE69514398D1 (de)	2000-02-17
PL181779B1 (pl)	2001-09-28
EG21121A (en)	2000-11-29
ATE188705T1 (de)	2000-01-15
ZA952649B (en)	1995-12-21
ES2143004T3 (es)	2000-05-01
CN1058011C (zh)	2000-11-01
HK1012002A1 (en)	1999-07-23
KR950032204A (ko)	1995-12-20
KR100221823B1 (ko)	1999-09-15
RU2109744C1 (ru)	1998-04-27
AP563A (en)	1996-11-21
US5614470A (en)	1997-03-25
AP9500727A0 (en)	1995-04-30
MX9501622A (es)	1997-03-29
IL113195A0 (en)	1995-06-29
CN1112119A (zh)	1995-11-22
GR3032847T3 (en)	2000-07-31
AU1620395A (en)	1995-10-12
TW305745B (pl)	1997-05-21
HU9500945D0 (en)	1995-05-29
EP0675133B1 (en)	2000-01-12
DE69514398T2 (de)	2000-08-31
AU682439B2 (en)	1997-10-02
PL307949A1 (en)	1995-10-02
RU95104884A (ru)	1996-12-20
HU215078B (hu)	1998-09-28
CA2146047A1 (en)	1995-10-02
DK0675133T3 (da)	2000-04-25
NZ270850A (en)	1996-03-26

Publication	Publication Date	Title
RU2049785C1 (ru)	1995-12-10	Макролидные соединения или их соли, или их сложные эфиры
US5614470A (en)	1997-03-25	13-substituted milbemycin derivatives, their preparation and their use
IE832762L (en)	1984-05-25	Didehydromilbemycin derivatives
KR100300376B1 (ko)	2001-10-22	13-치환밀베마이신5-옥심유도체,그의제조방법및곤충및기타해충에대한그의용도
EP3344612A1 (en)	2018-07-11	Spinosyn derivatives as insecticides
CA1235693A (en)	1988-04-26	Milbemycin 5-carbonate derivatives, their preparation and compositions containing them
JP3499097B2 (ja)	2004-02-23	１３位にオキシム基を含んだ置換基を有する殺虫性ミルベマイシン誘導体
CA2037414A1 (en)	1991-09-02	13-ether-substituted milbemycin derivatives
HUP0301040A2 (hu)	2003-08-28	Parazitaölő hatású 13 -szubsztituált milbemicinszármazékok, ezeket tartalmazó készítmények és alkalmazásuk
CN110256414A (zh)	2019-09-20	具有杀虫活性的二硫环戊烯酮类化合物及其合成
JP3499037B2 (ja)	2004-02-23	１３位にオキシム基を含んだ置換基を有する殺虫性ミルベマイシン誘導体
US5686484A (en)	1997-11-11	Milbemycin derivatives, their preparation and their use
CH620338A5 (pl)	1980-11-28
HK1012002B (en)	2001-02-23	13-substituted milbemycin derivatives, their preparation and use
JP3689462B2 (ja)	2005-08-31	殺虫活性を有する１３位置換ミルベマイシン誘導体
JP3762465B2 (ja)	2006-04-05	殺虫活性を有する１３位エーテル置換ミルベマイシン誘導体
DK171255B1 (da)	1996-08-12	Makrolidforbindelser, præparater indeholdende forbindelser til anvendelse i human medicin, veterinær medicin, og præparat til kontrol af skadedyr, ikke-terapeutisk fremgangsmåde til bekæmpelse af skadedyr samt fremgangsmåde til fremstilling af forbindelserne
JP3762460B2 (ja)	2006-04-05	１３位置換ミルベマイシン誘導体
JPH0370710B2 (pl)	1991-11-08
EP0060955A1 (fr)	1982-09-29	Nouveaux uraciles substitués comportant un groupement 2-tétra-hydropyranyle, leur procédé de préparation et les compositions pesticides les renfermant
WO1996016064A1 (en)	1996-05-30	13-etherified milbemycin derivative with insecticidal activity
JPH09151188A (ja)	1997-06-10	１３位置換ミルベマイシン５−オキシム誘導体
JPH1017568A (ja)	1998-01-20	新規マクロライド化合物
JPH06345771A (ja)	1994-12-20	新規１３−置換ミルベマイシン誘導体
JP2002012595A (ja)	2002-01-15	ミルベマイシン誘導体