CA2368465A1 - Avermectin derivatives - Google Patents

Avermectin derivatives Download PDF

Info

Publication number: CA2368465A1
Authority: CA; Canada
Prior art keywords: formula; compounds; spp; methyl; hydroxyl
Prior art date: 1999-03-25
Legal status (The legal status 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 status listed.): Abandoned

Application number

CA002368465A

Other languages

English (en)

French (fr)

Inventor

Werner Hallenbach

Achim Harder

Andreas Turberg

Olaf Hansen

Georg Von Samson-Himmelstjerna

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Individual

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.)

1999-03-25

Filing date

2000-03-13

Publication date

2000-10-05

2000-03-13 Application filed by Individual filed Critical Individual

2000-10-05 Publication of CA2368465A1 publication Critical patent/CA2368465A1/en

Status Abandoned legal-status Critical Current

Links

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 title abstract description 12
238000000034 method Methods 0.000 claims abstract description 44
241001465754 Metazoa Species 0.000 claims abstract description 18
244000079386 endoparasite Species 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims description 116
-1 hydroximino Chemical group 0.000 claims description 77
239000000203 mixture Substances 0.000 claims description 55
238000002360 preparation method Methods 0.000 claims description 44
238000006243 chemical reaction Methods 0.000 claims description 36
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 34
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
150000001412 amines Chemical class 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
125000006239 protecting group Chemical group 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
239000012279 sodium borohydride Substances 0.000 claims description 8
229910000033 sodium borohydride Inorganic materials 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000005842 heteroatom Chemical group 0.000 claims description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
239000005864 Sulphur Substances 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000003282 alkyl amino group Chemical group 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical group 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
150000008049 diazo compounds Chemical class 0.000 claims description 4
239000004606 Fillers/Extenders Substances 0.000 claims description 3
239000013543 active substance Substances 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 abstract description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 57
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 56
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
ZFUKERYTFURFGA-PVVXTEPVSA-N avermectin B1b 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 ZFUKERYTFURFGA-PVVXTEPVSA-N 0.000 description 30
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 29
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 17
239000002904 solvent Substances 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
150000003254 radicals Chemical class 0.000 description 13
238000012360 testing method Methods 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 12
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 11
239000000047 product Substances 0.000 description 11
239000005660 Abamectin Substances 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
239000003054 catalyst Substances 0.000 description 10
238000009472 formulation Methods 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
150000002170 ethers Chemical class 0.000 description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
235000014113 dietary fatty acids Nutrition 0.000 description 8
229960001760 dimethyl sulfoxide Drugs 0.000 description 8
239000000194 fatty acid Substances 0.000 description 8
229930195729 fatty acid Natural products 0.000 description 8
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
150000001298 alcohols Chemical class 0.000 description 7
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 7
150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
239000003085 diluting agent Substances 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
241000255925 Diptera Species 0.000 description 6
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
230000000694 effects Effects 0.000 description 6
150000004665 fatty acids Chemical class 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
239000007858 starting material Substances 0.000 description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
229920000151 polyglycol Polymers 0.000 description 5
239000010695 polyglycol Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
238000010626 work up procedure Methods 0.000 description 5
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
235000011054 acetic acid Nutrition 0.000 description 4
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CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
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238000000746 purification Methods 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
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NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 3
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NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
229960002447 thiram Drugs 0.000 description 1
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
229940074152 thuringiensin Drugs 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
JWXZLCFGVKMEEK-UHFFFAOYSA-N triarathene Chemical compound C1=CC(Cl)=CC=C1C1=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)S1 JWXZLCFGVKMEEK-UHFFFAOYSA-N 0.000 description 1
IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
PTMFUWGXPRYYMC-UHFFFAOYSA-N triethylazanium;formate Chemical compound OC=O.CCN(CC)CC PTMFUWGXPRYYMC-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 1
HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
241000701447 unidentified baculovirus Species 0.000 description 1
241000701366 unidentified nuclear polyhedrosis viruses Species 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000001993 wax Substances 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000005943 zeta-Cypermethrin Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Tropical Medicine & Parasitology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

CA002368465A 1999-03-25 2000-03-13 Avermectin derivatives Abandoned CA2368465A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19913534.7		1999-03-25
DE19913534A DE19913534A1 (de)	1999-03-25	1999-03-25	Avermectinderivate
PCT/EP2000/002189 WO2000058328A2 (de)	1999-03-25	2000-03-13	Avermectinderivate

Publications (1)

Publication Number	Publication Date
CA2368465A1 true CA2368465A1 (en)	2000-10-05

Family

ID=7902359

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002368465A Abandoned CA2368465A1 (en)	1999-03-25	2000-03-13	Avermectin derivatives

Country Status (9)

Country	Link
EP (1)	EP1169328A2 (pt)
JP (1)	JP2002540214A (pt)
CN (1)	CN1345327A (pt)
AU (1)	AU4394700A (pt)
BR (1)	BR0009285A (pt)
CA (1)	CA2368465A1 (pt)
DE (1)	DE19913534A1 (pt)
HK (1)	HK1045698A1 (pt)
WO (1)	WO2000058328A2 (pt)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10112318A1 (de) *	2001-02-05	2002-08-14	Henkel Kgaa	Konditioniermittel
CN102578113A (zh) *	2012-01-18	2012-07-18	华南理工大学	蔗糖酯与甲维盐复配微胶囊杀虫剂及其制备方法
JO3626B1 (ar)	2012-02-23	2020-08-27	Merial Inc	تركيبات موضعية تحتوي على فيبرونيل و بيرميثرين و طرق استخدامها
CN103601776A (zh) *	2013-11-25	2014-02-26	京博农化科技股份有限公司	一种甲维盐中间体的制备方法
CN103833811A (zh) *	2014-03-25	2014-06-04	武汉大学	一种阿维菌素衍生物及其制备方法
CN109824745A (zh) *	2019-01-24	2019-05-31	南开大学	一种伊维菌素衍生物的合成及应用
CN113817008B (zh) *	2021-07-15	2023-05-23	湖州师范学院	新型琥珀酰基十六元大环内酯的制备方法及用途

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES8800986A1 (es) *	1985-07-27	1987-12-01	Pfizer	Un procedimiento para la produccion de un nuevo derivado de avermectina
CH669382A5 (en) *	1986-05-21	1989-03-15	Ciba Geigy Ag	13-0-substd. milbemycin derivs. - with insecticidal, acaricidal, nematocidal and anthelmintic activity, prepd. by etherification of 13-0 unsubstituted cpds
GB8807280D0 (en) *	1988-03-26	1988-04-27	Pfizer Ltd	Antiparasitic agents

1999
- 1999-03-25 DE DE19913534A patent/DE19913534A1/de not_active Withdrawn
2000
- 2000-03-13 JP JP2000608028A patent/JP2002540214A/ja active Pending
- 2000-03-13 BR BR0009285-1A patent/BR0009285A/pt not_active IP Right Cessation
- 2000-03-13 CA CA002368465A patent/CA2368465A1/en not_active Abandoned
- 2000-03-13 EP EP00925111A patent/EP1169328A2/de not_active Withdrawn
- 2000-03-13 AU AU43947/00A patent/AU4394700A/en not_active Abandoned
- 2000-03-13 WO PCT/EP2000/002189 patent/WO2000058328A2/de not_active Application Discontinuation
- 2000-03-13 CN CN00805507A patent/CN1345327A/zh active Pending
2002
- 2002-10-07 HK HK02107331.1A patent/HK1045698A1/zh unknown

Also Published As

Publication number	Publication date
CN1345327A (zh)	2002-04-17
WO2000058328A2 (de)	2000-10-05
HK1045698A1 (zh)	2002-12-06
WO2000058328A3 (de)	2001-04-26
DE19913534A1 (de)	2000-10-05
BR0009285A (pt)	2002-01-22
EP1169328A2 (de)	2002-01-09
AU4394700A (en)	2000-10-16
JP2002540214A (ja)	2002-11-26

Publication	Publication Date	Title
EP2862872A1 (en)	2015-04-22	Novel cyclic depsipeptide derivative and pest control agent comprising same
CA2242905A1 (en)	1997-07-24	Acylated 5-amino-1,2,4-thiadiazoles as pesticides and fungicides
CA2368465A1 (en)	2000-10-05	Avermectin derivatives
US6127364A (en)	2000-10-03	1,3,4-oxadiazine derivatives and their use as pesticides
US6710045B2 (en)	2004-03-23	Heterocyclic fluoroalkenyl thioethers and the use thereof as pesticides (IV)
US6908937B2 (en)	2005-06-21	Heterocyclic fluoroalkenyl thioethers (II)
US7645738B2 (en)	2010-01-12	18-membered nitrobenzyl- and aminobenzyl-substituted cyclohexadepsipeptides for controlling endoparasites and a process for their preparation
WO2005026139A1 (en)	2005-03-24	Nematicidal difluoroalkenes
US6927215B2 (en)	2005-08-09	Heterocyclic fluoroalkenyl thioethers and the use thereof as pesticides (I)
US20040106658A1 (en)	2004-06-03	Heterocyclic fluoroalkenyl thioethers and the use thereof as pesticides(III)
AU768501B2 (en)	2003-12-11	Cyclo-imino depsipeptides and their utilization in controlling endoparasites
WO2001040256A1 (en)	2001-06-07	Taccalonolides and their use
WO2002050042A2 (de)	2002-06-27	Verwendung von pyrazoloxim-mischungen als parasitizide mittel

Legal Events

Date	Code	Title	Description
2005-03-14	FZDE	Dead