IL104171A - History 31 -]) Tharoylthio (alkanoylloxy [milbemycin, parasiticides containing them, processes for their preparation and methods of plant protection using - Google Patents

History 31 -]) Tharoylthio (alkanoylloxy [milbemycin, parasiticides containing them, processes for their preparation and methods of plant protection using

Info

Publication number: IL104171A
Authority: IL; Israel
Prior art keywords: group; groups; methyl; atoms; ethyl
Prior art date: 1991-12-18

Application number

IL10417192A

Other languages

English (en)

Hebrew (he)

Other versions

IL104171A0 (en

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.)

1991-12-18

Filing date

1992-12-18

Publication date

1996-10-31

1992-12-18 Application filed by Sankyo Co filed Critical Sankyo Co

1993-05-13 Publication of IL104171A0 publication Critical patent/IL104171A0/xx

1996-10-31 Publication of IL104171A publication Critical patent/IL104171A/en

Links

239000000203 mixture Substances 0.000 title claims description 76
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 description 64
238000000034 method Methods 0.000 title claims description 33
238000002360 preparation method Methods 0.000 title description 8
230000000590 parasiticidal effect Effects 0.000 title description 2
125000004423 acyloxy group Chemical group 0.000 title 1
125000005368 heteroarylthio group Chemical group 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 276
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 46
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 46
125000000217 alkyl group Chemical group 0.000 claims abstract description 24
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 23
125000003118 aryl group Chemical group 0.000 claims abstract description 18
150000003839 salts Chemical class 0.000 claims abstract description 18
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 17
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 17
125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 16
230000000895 acaricidal effect Effects 0.000 claims abstract description 12
230000000507 anthelmentic effect Effects 0.000 claims abstract description 10
125000004981 cycloalkylmethyl group Chemical group 0.000 claims abstract description 8
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 8
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
-1 1, 3-benzodioxolan-5-yl group Chemical group 0.000 claims description 159
125000004432 carbon atom Chemical group C* 0.000 claims description 65
125000001424 substituent group Chemical group 0.000 claims description 37
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 21
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 20
125000001309 chloro group Chemical group Cl* 0.000 claims description 16
125000005843 halogen group Chemical group 0.000 claims description 16
125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 13
125000001153 fluoro group Chemical group F* 0.000 claims description 13
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
125000003277 amino group Chemical group 0.000 claims description 12
241000238631 Hexapoda Species 0.000 claims description 11
230000000749 insecticidal effect Effects 0.000 claims description 11
244000045947 parasite Species 0.000 claims description 11
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 10
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 8
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 7
125000002723 alicyclic group Chemical group 0.000 claims description 7
125000004430 oxygen atom Chemical group O* 0.000 claims description 7
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 7
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 5
125000002837 carbocyclic group Chemical group 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
238000002474 experimental method Methods 0.000 claims description 4
244000000013 helminth Species 0.000 claims description 4
230000001850 reproductive effect Effects 0.000 claims description 4
125000005002 aryl methyl group Chemical group 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
125000001188 haloalkyl group Chemical group 0.000 claims description 3
125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 claims description 3
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 1
239000001257 hydrogen Substances 0.000 abstract description 11
229910052739 hydrogen Inorganic materials 0.000 abstract description 11
239000002917 insecticide Substances 0.000 abstract description 4
125000000446 sulfanediyl group Chemical class *S* 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 87
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 76
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
238000001819 mass spectrum Methods 0.000 description 69
239000002904 solvent Substances 0.000 description 41
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
239000002253 acid Substances 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
239000003153 chemical reaction reagent Substances 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
239000000243 solution Substances 0.000 description 15
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
239000007864 aqueous solution Substances 0.000 description 13
230000000694 effects Effects 0.000 description 13
239000004495 emulsifiable concentrate Substances 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
150000001732 carboxylic acid derivatives Chemical group 0.000 description 12
239000000126 substance Substances 0.000 description 12
241000196324 Embryophyta Species 0.000 description 11
241001465754 Metazoa Species 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
230000003287 optical effect Effects 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
238000004821 distillation Methods 0.000 description 9
239000003480 eluent Substances 0.000 description 9
ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical class 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 description 9
229920006395 saturated elastomer Polymers 0.000 description 9
239000011780 sodium chloride Substances 0.000 description 9
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 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
231100000989 no adverse effect Toxicity 0.000 description 8
230000001473 noxious effect Effects 0.000 description 8
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 8
239000008096 xylene Substances 0.000 description 8
229910021595 Copper(I) iodide Inorganic materials 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 7
239000003120 macrolide antibiotic agent Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
238000010828 elution Methods 0.000 description 6
150000002170 ethers Chemical class 0.000 description 6
239000000843 powder Substances 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
239000003638 chemical reducing agent Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
SBTSVTLGWRLWOD-UHFFFAOYSA-L copper(ii) triflate Chemical compound [Cu+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F SBTSVTLGWRLWOD-UHFFFAOYSA-L 0.000 description 5
238000009472 formulation Methods 0.000 description 5
229940098779 methanesulfonic acid Drugs 0.000 description 5
239000012279 sodium borohydride Substances 0.000 description 5
229910000033 sodium borohydride Inorganic materials 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
239000000969 carrier Substances 0.000 description 4
230000003197 catalytic effect Effects 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
150000008282 halocarbons Chemical class 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
150000002484 inorganic compounds Chemical class 0.000 description 4
229910010272 inorganic material Inorganic materials 0.000 description 4
239000007788 liquid Substances 0.000 description 4
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 description 4
230000003071 parasitic effect Effects 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000000047 product Substances 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
125000006413 ring segment Chemical group 0.000 description 4
238000010898 silica gel chromatography Methods 0.000 description 4
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 4
239000007858 starting material Substances 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
UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 4
SPXOTSHWBDUUMT-UHFFFAOYSA-N 138-42-1 Chemical compound OS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-N 0.000 description 3
241000175828 Adoxophyes orana Species 0.000 description 3
102000052583 Anaphase-Promoting Complex-Cyclosome Apc8 Subunit Human genes 0.000 description 3
206010049119 Emotional distress Diseases 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
101000912124 Homo sapiens Cell division cycle protein 23 homolog Proteins 0.000 description 3
BWCRYQGQPDBOAU-UHFFFAOYSA-N Milbemycin D Natural products C1CC(C)C(C(C)C)OC21OC(CC=C(C)CC(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 BWCRYQGQPDBOAU-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
241000500439 Plutella Species 0.000 description 3
239000004698 Polyethylene Substances 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
241000985245 Spodoptera litura Species 0.000 description 3
235000011054 acetic acid Nutrition 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
239000000654 additive Substances 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 3
229940092714 benzenesulfonic acid Drugs 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 3
230000009429 distress Effects 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
125000005948 methanesulfonyloxy group Chemical group 0.000 description 3
244000005700 microbiome Species 0.000 description 3
BWCRYQGQPDBOAU-WZBVPYLGSA-N milbemycin D Chemical compound C1C[C@H](C)[C@@H](C(C)C)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 BWCRYQGQPDBOAU-WZBVPYLGSA-N 0.000 description 3
150000002825 nitriles Chemical class 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
230000000361 pesticidal effect Effects 0.000 description 3
229920000573 polyethylene Polymers 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 3
230000009257 reactivity Effects 0.000 description 3
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150000003462 sulfoxides Chemical class 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
208000024891 symptom Diseases 0.000 description 3
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WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
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VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
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229910021532 Calcite Inorganic materials 0.000 description 2
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
241001126268 Cooperia Species 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
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QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
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VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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241000500891 Insecta Species 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
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241001137882 Nematodirus Species 0.000 description 2
241000510960 Oesophagostomum Species 0.000 description 2
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BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
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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
PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000000640 hydroxylating effect Effects 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
238000002347 injection Methods 0.000 description 1
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239000002198 insoluble material Substances 0.000 description 1
238000007689 inspection Methods 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
150000008040 ionic compounds Chemical class 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 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
239000004310 lactic acid Substances 0.000 description 1
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229960000448 lactic acid Drugs 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
244000144972 livestock Species 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
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235000019359 magnesium stearate Nutrition 0.000 description 1
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235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000012764 mineral filler Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
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ULWOJODHECIZAU-UHFFFAOYSA-N n,n-diethylpropan-2-amine Chemical compound CCN(CC)C(C)C ULWOJODHECIZAU-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
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125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
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150000007530 organic bases Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
229940116315 oxalic acid Drugs 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
206010033675 panniculitis Diseases 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
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 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
238000004525 petroleum distillation Methods 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
230000000704 physical effect Effects 0.000 description 1
239000006187 pill Substances 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
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
ONQDVAFWWYYXHM-UHFFFAOYSA-M potassium lauryl sulfate Chemical compound [K+].CCCCCCCCCCCCOS([O-])(=O)=O ONQDVAFWWYYXHM-UHFFFAOYSA-M 0.000 description 1
229940116985 potassium lauryl sulfate Drugs 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
244000144977 poultry Species 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
210000000253 proventriculus Anatomy 0.000 description 1
239000008262 pumice Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 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
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 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
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
210000004304 subcutaneous tissue Anatomy 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 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)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Environmental Sciences (AREA)
Molecular Biology (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Plant Pathology (AREA)
Pest Control & Pesticides (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Dentistry (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Saccharide Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

IL10417192A 1991-12-18 1992-12-18 History 31 -]) Tharoylthio (alkanoylloxy [milbemycin, parasiticides containing them, processes for their preparation and methods of plant protection using IL104171A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP33465091		1991-12-18

Publications (2)

Publication Number	Publication Date
IL104171A0 IL104171A0 (en)	1993-05-13
IL104171A true IL104171A (en)	1996-10-31

Family

ID=18279733

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10417192A IL104171A (en)	1991-12-18	1992-12-18	History 31 -]) Tharoylthio (alkanoylloxy [milbemycin, parasiticides containing them, processes for their preparation and methods of plant protection using

Country Status (20)

Country	Link
US (1)	US5276033A (fr)
EP (1)	EP0549273B1 (fr)
JP (1)	JP3087987B2 (fr)
KR (1)	KR0171426B1 (fr)
CN (1)	CN1039645C (fr)
AT (1)	ATE163419T1 (fr)
AU (1)	AU658037B2 (fr)
CA (1)	CA2085703C (fr)
DE (1)	DE69224508T2 (fr)
DK (1)	DK0549273T3 (fr)
EG (1)	EG19869A (fr)
ES (1)	ES2114551T3 (fr)
HU (1)	HU217303B (fr)
IL (1)	IL104171A (fr)
LV (1)	LV12132B (fr)
MX (1)	MX9207464A (fr)
NZ (1)	NZ245533A (fr)
RU (1)	RU2086552C1 (fr)
UA (1)	UA44886C2 (fr)
ZA (1)	ZA929882B (fr)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0342710B1 (fr) *	1986-03-25	1993-05-19	Sankyo Company Limited	Dérivés du type macrolide, leur préparation et leur utilisation
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
US5614470A (en) *	1994-04-01	1997-03-25	Sankyo Company, Limited	13-substituted milbemycin derivatives, their preparation and their use
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
FR2780409B1 (fr) *	1998-06-30	2001-07-13	Omya Sa	Procede pour traiter une charge minerale par un phosphate, charge minerale ainsi traitee, mousses de polyurethanne et polyurethannes composites utilisant cette charge, objets moules ou non les contenant
CA2464403A1 (fr) *	2001-10-25	2003-05-01	Novartis Animal Health K.K.	Composition anthelmintique
EP1849363A1 (fr) *	2006-03-09	2007-10-31	Cheminova A/S	Combinations synergiques d'un plaguicide agoniste des canaux à chlorure actives par le glutamate ou le GABA et au moins un d'entre la vitamine E et la niacin
RU2554074C1 (ru) *	2014-04-18	2015-06-27	Игорь Викторович Заварзин	Антипаразитарный агент

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3950360A (en) *	1972-06-08	1976-04-13	Sankyo Company Limited	Antibiotic substances
US4206205A (en) *	1977-10-03	1980-06-03	Merck & Co., Inc.	Monosaccharide and aglycone derivatives of C-076
US4201861A (en) *	1977-10-03	1980-05-06	Merck & Co., Inc.	Acyl derivatives of C-076 compounds
US4173571A (en) *	1977-12-19	1979-11-06	Merck & Co., Inc.	13-Halo and 13-deoxy derivatives of C-076 compounds
US4171314A (en) *	1977-12-19	1979-10-16	Merck & Co., Inc.	13-Halo and 13-deoxy C-076 compounds
US4203976A (en) *	1978-08-02	1980-05-20	Merck & Co., Inc.	Sugar derivatives of C-076 compounds
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
US4289760A (en) *	1980-05-02	1981-09-15	Merck & Co., Inc.	23-Keto derivatives of C-076 compounds
US4457920A (en) *	1981-09-03	1984-07-03	Merck & Co., Inc.	4a-Substituted avermectin compounds
US4423209A (en) *	1982-02-26	1983-12-27	Merck & Co., Inc.	Processes for the interconversion of avermectin compounds
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
US4579864A (en) *	1984-06-11	1986-04-01	Merck & Co., Inc.	Avermectin and milbemycin 13-keto, 13-imino and 13-amino derivatives
US4547491A (en) *	1984-07-18	1985-10-15	Merck & Co., Inc.	C-8A-Oxo-avermectin and milbemycin derivatives, pharmaceutical compositions and method of use
US4696922A (en) *	1984-11-26	1987-09-29	Ciba-Geigy Corporation	5-azolylacetoxymilbemycins as ecto- and endoparasites
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
EP0342710B1 (fr) *	1986-03-25	1993-05-19	Sankyo Company Limited	Dérivés du type macrolide, leur préparation et leur utilisation
JPH0826026B2 (ja) *	1986-06-13	1996-03-13	三共株式会社	ミルベマイシン類の１３−エステル誘導体およびその用途
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
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

1992
- 1992-12-17 RU RU92016232/04A patent/RU2086552C1/ru not_active IP Right Cessation
- 1992-12-17 KR KR1019920024697A patent/KR0171426B1/ko not_active Expired - Fee Related
- 1992-12-17 EG EG78792A patent/EG19869A/xx active
- 1992-12-17 CA CA002085703A patent/CA2085703C/fr not_active Expired - Fee Related
- 1992-12-17 US US07/992,865 patent/US5276033A/en not_active Expired - Fee Related
- 1992-12-18 EP EP92311581A patent/EP0549273B1/fr not_active Expired - Lifetime
- 1992-12-18 AU AU30312/92A patent/AU658037B2/en not_active Ceased
- 1992-12-18 NZ NZ245533A patent/NZ245533A/xx unknown
- 1992-12-18 DE DE69224508T patent/DE69224508T2/de not_active Expired - Fee Related
- 1992-12-18 ES ES92311581T patent/ES2114551T3/es not_active Expired - Lifetime
- 1992-12-18 IL IL10417192A patent/IL104171A/en not_active IP Right Cessation
- 1992-12-18 DK DK92311581T patent/DK0549273T3/da active
- 1992-12-18 ZA ZA929882A patent/ZA929882B/xx unknown
- 1992-12-18 HU HU9204023A patent/HU217303B/hu not_active IP Right Cessation
- 1992-12-18 AT AT92311581T patent/ATE163419T1/de not_active IP Right Cessation
- 1992-12-18 JP JP04338308A patent/JP3087987B2/ja not_active Expired - Fee Related
- 1992-12-18 CN CN92115349A patent/CN1039645C/zh not_active Expired - Fee Related
- 1992-12-18 MX MX9207464A patent/MX9207464A/es unknown
1993
- 1993-06-18 UA UA93003130A patent/UA44886C2/uk unknown
1998
- 1998-07-02 LV LVP-98-140A patent/LV12132B/en unknown

Also Published As

Publication number	Publication date
IL104171A0 (en)	1993-05-13
ES2114551T3 (es)	1998-06-01
CA2085703C (fr)	2001-05-01
HUT64073A (en)	1993-11-29
HU217303B (hu)	1999-12-28
JPH05255343A (ja)	1993-10-05
KR0171426B1 (ko)	1999-02-01
MX9207464A (es)	1993-07-30
DE69224508D1 (de)	1998-04-02
HU9204023D0 (en)	1993-04-28
DE69224508T2 (de)	1998-10-15
RU2086552C1 (ru)	1997-08-10
KR930012786A (ko)	1993-07-21
NZ245533A (en)	1995-07-26
US5276033A (en)	1994-01-04
HK1007658A1 (en)	1999-04-16
DK0549273T3 (da)	1998-11-23
ZA929882B (en)	1993-06-24
AU658037B2 (en)	1995-03-30
EP0549273A1 (fr)	1993-06-30
AU3031292A (en)	1993-06-24
EP0549273B1 (fr)	1998-02-25
EG19869A (en)	1996-03-31
JP3087987B2 (ja)	2000-09-18
LV12132B (en)	1998-12-20
CN1039645C (zh)	1998-09-02
LV12132A (lv)	1998-09-20
ATE163419T1 (de)	1998-03-15
CN1074445A (zh)	1993-07-21
UA44886C2 (uk)	2002-03-15
CA2085703A1 (fr)	1993-06-19

Legal Events

Date	Code	Title
1997-03-18	FF	Patent granted
1997-11-20	KB	Patent renewed
2003-02-12	KB	Patent renewed
2007-08-19	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
US4696945A (en)	1987-09-29	13β-milbemycin derivatives for controlling ecto- and endoparasites of plants and animals
EP0342710B1 (fr)	1993-05-19	Dérivés du type macrolide, leur préparation et leur utilisation
KR960001480B1 (ko)	1996-01-31	농약으로서 유용한 13β-밀베마이신 유도체
CA1261824A (fr)	1989-09-26	Pesticides
RU2109744C1 (ru)	1998-04-27	13-замещенные производные милбемицина, акарицидная и инсектицидная композиция и способ защиты растений от повреждения паразитами
US5276033A (en)	1994-01-04	13-(substituted thio)acetoxymilbemycin derivatives, their preparation and their agrochemical uses
EP1276748B1 (fr)	2006-01-11	Derives de milbemycine substitues en position 13, leur preparation et leur utilisation contre les insectes et autres parasites
CA1242436A (fr)	1988-09-27	Derive de lactone, sa preparation, et son emploi pour la repression des insectes
HK1005731B (en)	1999-01-22	Milbemycin ether derivatives, their preparation and their therapeutic and agrochemical uses
AU2001252613A1 (en)	2002-01-31	13-substituted milbemycin derivatives, their preparation and their use against insects and other pests
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
HK1007658B (en)	1999-04-16	13-(substituted thio)acetoxymilbemycin derivatives, their preparation and their agrochemical uses
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
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
JP3762460B2 (ja)	2006-04-05	１３位置換ミルベマイシン誘導体
JPH1017568A (ja)	1998-01-20	新規マクロライド化合物
JPH06345769A (ja)	1994-12-20	ミルベマイシンマクロライド１３−エステル誘導体
JPH08193085A (ja)	1996-07-30	殺虫活性を有する１３位置換ミルベマイシン誘導体
JPS62221689A (ja)	1987-09-29	１３β−カルバモイルオキシミルベマイシン誘導体、その製造方法及び有害生物防除組成物
IE67058B1 (en)	1996-02-21	Macrolide compounds their preparation and their use