DK170822B1 - 23-Oxo- og -iminoderivater af LL-F28249-forbindel ser, deres anvendelse ved fremgangsmåder til bekæmpelse af skadelige insekter og plantenematoder samt midler indeholdende dem til bekæmpelse af insekter og af endo- og/eller ectoparasitter hos varmblodede dyr - Google Patents

23-Oxo- og -iminoderivater af LL-F28249-forbindel ser, deres anvendelse ved fremgangsmåder til bekæmpelse af skadelige insekter og plantenematoder samt midler indeholdende dem til bekæmpelse af insekter og af endo- og/eller ectoparasitter hos varmblodede dyr Download PDF

Info

Publication number: DK170822B1
Authority: DK; Denmark
Prior art keywords: compounds; isopropyl; oxo; ethyl; control
Prior art date: 1986-09-12

Application number

DK475587A

Other languages

Danish (da)

English (en)

Other versions

DK475587D0 (da

DK475587A (da

Inventor

Goro Asato

Donald John France

Original Assignee

American Cyanamid 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.)

1986-09-12

Filing date

1987-09-11

Publication date

1996-01-29

1987-09-11 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1987-09-11 Publication of DK475587D0 publication Critical patent/DK475587D0/da

1988-03-13 Publication of DK475587A publication Critical patent/DK475587A/da

1996-01-29 Application granted granted Critical

1996-01-29 Publication of DK170822B1 publication Critical patent/DK170822B1/da

Links

150000001875 compounds Chemical class 0.000 title claims description 68
241001465754 Metazoa Species 0.000 title claims description 28
238000000034 method Methods 0.000 title claims description 16
241000238631 Hexapoda Species 0.000 title claims description 13
-1 gents Species 0.000 title description 13
125000001841 imino group Chemical group [H]N=* 0.000 title description 3
239000008280 blood Substances 0.000 title description 2
210000004369 blood Anatomy 0.000 title description 2
241000341511 Nematodes Species 0.000 title 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
238000011282 treatment Methods 0.000 claims description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
241000244206 Nematoda Species 0.000 claims description 7
244000078703 ectoparasite Species 0.000 claims description 7
230000002265 prevention Effects 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
239000002689 soil Substances 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
208000015181 infectious disease Diseases 0.000 claims description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
230000001069 nematicidal effect Effects 0.000 claims 1
230000000069 prophylactic effect Effects 0.000 claims 1
230000009885 systemic effect Effects 0.000 claims 1
230000000699 topical effect Effects 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
239000000203 mixture Substances 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
244000045947 parasite Species 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 9
239000010410 layer Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
238000004128 high performance liquid chromatography Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
238000004949 mass spectrometry Methods 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
125000006239 protecting group Chemical group 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
241000282412 Homo Species 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
201000010099 disease Diseases 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
241000238876 Acari Species 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
241000196324 Embryophyta Species 0.000 description 4
208000006968 Helminthiasis Diseases 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
208000030852 Parasitic disease Diseases 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
235000013312 flour Nutrition 0.000 description 4
210000001035 gastrointestinal tract Anatomy 0.000 description 4
244000000013 helminth Species 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
208000014837 parasitic helminthiasis infectious disease Diseases 0.000 description 4
239000000047 product Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
210000001519 tissue Anatomy 0.000 description 4
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
241000255925 Diptera Species 0.000 description 3
206010061217 Infestation Diseases 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
241000187747 Streptomyces Species 0.000 description 3
230000000895 acaricidal effect Effects 0.000 description 3
239000000642 acaricide Substances 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000003242 anti bacterial agent Substances 0.000 description 3
229940088710 antibiotic agent Drugs 0.000 description 3
229940125773 compound 10 Drugs 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000000855 fermentation Methods 0.000 description 3
230000004151 fermentation Effects 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
239000007788 liquid Substances 0.000 description 3
244000005700 microbiome Species 0.000 description 3
210000000056 organ Anatomy 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000001632 sodium acetate Substances 0.000 description 3
235000017281 sodium acetate Nutrition 0.000 description 3
239000002904 solvent Substances 0.000 description 3
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
241001147657 Ancylostoma Species 0.000 description 2
241000238421 Arthropoda Species 0.000 description 2
241000244186 Ascaris Species 0.000 description 2
241000283690 Bos taurus Species 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
241000253350 Capillaria Species 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
241001126268 Cooperia Species 0.000 description 2
241001147667 Dictyocaulus Species 0.000 description 2
241000283086 Equidae Species 0.000 description 2
241000243976 Haemonchus Species 0.000 description 2
108010034145 Helminth Proteins Proteins 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
241001137882 Nematodirus Species 0.000 description 2
JWIPGAFCGUDKEY-UHFFFAOYSA-L O[Cr](Cl)(=O)=O.C1=CC=NC=C1 Chemical compound O[Cr](Cl)(=O)=O.C1=CC=NC=C1 JWIPGAFCGUDKEY-UHFFFAOYSA-L 0.000 description 2
241000243795 Ostertagia Species 0.000 description 2
241001494479 Pecora Species 0.000 description 2
241001674048 Phthiraptera Species 0.000 description 2
241000283984 Rodentia Species 0.000 description 2
241000258242 Siphonaptera Species 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
241000244174 Strongyloides Species 0.000 description 2
241000243774 Trichinella Species 0.000 description 2
241001489151 Trichuris Species 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
230000000507 anthelmentic effect Effects 0.000 description 2
239000000921 anthelmintic agent Substances 0.000 description 2
229940124339 anthelmintic agent Drugs 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
235000011089 carbon dioxide Nutrition 0.000 description 2
239000000969 carrier Substances 0.000 description 2
235000005822 corn Nutrition 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 2
239000002917 insecticide Substances 0.000 description 2
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 2
244000144972 livestock Species 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
239000000463 material Substances 0.000 description 2
230000001617 migratory effect Effects 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000002808 molecular sieve Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
230000036281 parasite infection Effects 0.000 description 2
244000144977 poultry Species 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000008107 starch Substances 0.000 description 2
239000013589 supplement Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 1
SKIIKRJAQOSWFT-UHFFFAOYSA-N 2-[3-[1-(2,2-difluoroethyl)piperidin-4-yl]oxy-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound FC(CN1CCC(CC1)OC1=NN(C=C1C=1C=NC(=NC=1)NC1CC2=CC=CC=C2C1)CC(=O)N1CC2=C(CC1)NN=N2)F SKIIKRJAQOSWFT-UHFFFAOYSA-N 0.000 description 1
241000254032 Acrididae Species 0.000 description 1
241000396431 Anthrenus scrophulariae Species 0.000 description 1
241001124076 Aphididae Species 0.000 description 1
241000204727 Ascaridia Species 0.000 description 1
241000760149 Aspiculuris Species 0.000 description 1
241000131286 Attagenus Species 0.000 description 1
241000238658 Blattella Species 0.000 description 1
241001674044 Blattodea Species 0.000 description 1
241000244036 Brugia Species 0.000 description 1
241000931178 Bunostomum Species 0.000 description 1
GRGYQFYKOTVFJT-UHFFFAOYSA-L CC1=CC(=NN1)C.[Cr](=O)(=O)(O)O Chemical compound CC1=CC(=NN1)C.[Cr](=O)(=O)(O)O GRGYQFYKOTVFJT-UHFFFAOYSA-L 0.000 description 1
241000283707 Capra Species 0.000 description 1
241000893172 Chabertia Species 0.000 description 1
241000207199 Citrus Species 0.000 description 1
241000254173 Coleoptera Species 0.000 description 1
241000692095 Cuterebra Species 0.000 description 1
244000000626 Daucus carota Species 0.000 description 1
235000002767 Daucus carota Nutrition 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
241000243990 Dirofilaria Species 0.000 description 1
235000003550 Dracunculus Nutrition 0.000 description 1
241000316827 Dracunculus <angiosperm> Species 0.000 description 1
241000498256 Enterobius Species 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
241001660203 Gasterophilus Species 0.000 description 1
241000256244 Heliothis virescens Species 0.000 description 1
241000257176 Hypoderma <fly> Species 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
235000019738 Limestone Nutrition 0.000 description 1
241000257162 Lucilia <blowfly> Species 0.000 description 1
208000002720 Malnutrition Diseases 0.000 description 1
241001143352 Meloidogyne Species 0.000 description 1
GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 description 1
241000257159 Musca domestica Species 0.000 description 1
241000498271 Necator Species 0.000 description 1
208000000291 Nematode infections Diseases 0.000 description 1
241000243981 Onchocerca Species 0.000 description 1
241000238814 Orthoptera Species 0.000 description 1
241000237502 Ostreidae Species 0.000 description 1
241000904715 Oxyuris Species 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
241000305186 Persectania ewingii Species 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
208000035415 Reinfection Diseases 0.000 description 1
241000122932 Strongylus Species 0.000 description 1
241000282887 Suidae Species 0.000 description 1
241000975704 Syphacia Species 0.000 description 1
241000254105 Tenebrio Species 0.000 description 1
241001454295 Tetranychidae Species 0.000 description 1
241001454294 Tetranychus Species 0.000 description 1
241000333689 Tineola Species 0.000 description 1
241000607216 Toxascaris Species 0.000 description 1
241000254086 Tribolium <beetle> Species 0.000 description 1
241000243797 Trichostrongylus Species 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
244000098338 Triticum aestivum Species 0.000 description 1
241000571986 Uncinaria Species 0.000 description 1
229920001938 Vegetable gum Polymers 0.000 description 1
241000244002 Wuchereria Species 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
208000007502 anemia Diseases 0.000 description 1
230000002141 anti-parasite Effects 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
239000003096 antiparasitic agent Substances 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
238000009395 breeding Methods 0.000 description 1
230000001488 breeding effect Effects 0.000 description 1
MXOSTENCGSDMRE-UHFFFAOYSA-N butyl-chloro-dimethylsilane Chemical compound CCCC[Si](C)(C)Cl MXOSTENCGSDMRE-UHFFFAOYSA-N 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
235000020971 citrus fruits Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000013058 crude material Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000006378 damage Effects 0.000 description 1
238000001212 derivatisation Methods 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000003651 drinking water Substances 0.000 description 1
235000020188 drinking water Nutrition 0.000 description 1
239000013057 ectoparasiticide Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
229940074076 glycerol formal Drugs 0.000 description 1
125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 description 1
208000035474 group of disease Diseases 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
230000007794 irritation Effects 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000006028 limestone Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
210000003563 lymphoid tissue Anatomy 0.000 description 1
239000003120 macrolide antibiotic agent Substances 0.000 description 1
229940041033 macrolides Drugs 0.000 description 1
230000001071 malnutrition Effects 0.000 description 1
235000000824 malnutrition Nutrition 0.000 description 1
238000003801 milling Methods 0.000 description 1
235000013379 molasses Nutrition 0.000 description 1
208000015380 nutritional deficiency disease Diseases 0.000 description 1
NUXCOKIYARRTDC-UHFFFAOYSA-N o-ethylhydroxylamine;hydron;chloride Chemical compound Cl.CCON NUXCOKIYARRTDC-UHFFFAOYSA-N 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
235000020636 oyster Nutrition 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
239000000575 pesticide Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000003223 protective agent Substances 0.000 description 1
210000003296 saliva Anatomy 0.000 description 1
230000009528 severe injury Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007892 solid unit dosage form Substances 0.000 description 1
RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
241000894007 species Species 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000007858 starting material Substances 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
239000000375 suspending agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
230000004580 weight loss Effects 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
- 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
- A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/195—Antibiotics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents

Landscapes

Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Zoology (AREA)
Pest Control & Pesticides (AREA)
Wood Science & Technology (AREA)
Polymers & Plastics (AREA)
Environmental Sciences (AREA)
Dentistry (AREA)
Veterinary Medicine (AREA)
Plant Pathology (AREA)
Agronomy & Crop Science (AREA)
Biochemistry (AREA)
Genetics & Genomics (AREA)
Public Health (AREA)
Biotechnology (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Tropical Medicine & Parasitology (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Insects & Arthropods (AREA)
General Chemical & Material Sciences (AREA)
Molecular Biology (AREA)
Animal Husbandry (AREA)
Pharmacology & Pharmacy (AREA)
Food Science & Technology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DK475587A 1986-09-12 1987-09-11 23-Oxo- og -iminoderivater af LL-F28249-forbindel ser, deres anvendelse ved fremgangsmåder til bekæmpelse af skadelige insekter og plantenematoder samt midler indeholdende dem til bekæmpelse af insekter og af endo- og/eller ectoparasitter hos varmblodede dyr DK170822B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US90728386A	1986-09-12	1986-09-12
US90728386		1986-09-12

Publications (3)

Publication Number	Publication Date
DK475587D0 DK475587D0 (da)	1987-09-11
DK475587A DK475587A (da)	1988-03-13
DK170822B1 true DK170822B1 (da)	1996-01-29

Family

ID=25423827

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK475587A DK170822B1 (da)	1986-09-12	1987-09-11	23-Oxo- og -iminoderivater af LL-F28249-forbindel ser, deres anvendelse ved fremgangsmåder til bekæmpelse af skadelige insekter og plantenematoder samt midler indeholdende dem til bekæmpelse af insekter og af endo- og/eller ectoparasitter hos varmblodede dyr

Country Status (17)

Country	Link
EP (1)	EP0259779B1 (hu)
JP (1)	JP2654028B2 (hu)
KR (1)	KR960004941B1 (hu)
AR (1)	AR246267A1 (hu)
AT (1)	ATE109783T1 (hu)
AU (1)	AU604749B2 (hu)
BR (1)	BR8704738A (hu)
CA (1)	CA1301164C (hu)
DE (1)	DE3750355T2 (hu)
DK (1)	DK170822B1 (hu)
ES (1)	ES2058082T3 (hu)
HU (1)	HU203239B (hu)
IE (1)	IE65147B1 (hu)
IL (1)	IL83796A0 (hu)
NZ (1)	NZ221714A (hu)
PT (1)	PT85674B (hu)
ZA (1)	ZA876832B (hu)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1296329C (en) *	1986-06-06	1992-02-25	Derek R. Sutherland	Macrolide compounds
US4806527A (en) *	1987-03-16	1989-02-21	Merck & Co., Inc.	Avermectin derivatives
GB8721374D0 (en) *	1987-09-11	1987-10-21	Glaxo Group Ltd	Chemical process
US5192777A (en) *	1987-09-11	1993-03-09	American Cyanamid Company	Macrolide compounds
GB8721377D0 (en) *	1987-09-11	1987-10-21	Glaxo Group Ltd	Chemical compounds
GB8811037D0 (en) *	1988-05-10	1988-06-15	Glaxo Group Ltd	Chemical compounds
JP2629047B2 (ja) *	1988-05-10	1997-07-09	アメリカン・サイアナミツド・カンパニー	マクロライド化合物
GB8811036D0 (en) *	1988-05-10	1988-06-15	Glaxo Group Ltd	Chemical compounds
ATE103173T1 (de) *	1989-02-28	1994-04-15	American Cyanamid Co	Bolus mit lang andauernder wirkstoffabgabe, wirksam bei der prophylaxe, behandlung oder bekaempfung des befalls bei wiederkaeuern durch fadenwuermer, milben und endo- und ektoparasiten.
NZ233680A (en) *	1989-05-17	1995-02-24	Beecham Group Plc	Avermectins and milbemycins and compositions thereof
US4988824A (en) *	1989-09-11	1991-01-29	Maulding Donald R	Process for the preparation of 23-(C1-C6 alkyloxime)-LL-F28249 compounds
EP0423445B1 (en) *	1989-09-11	1995-11-08	American Cyanamid Company	13-alkyl-23-imino and 13-halo-23-imino derivatives of LL-F28249 compounds and their use as endo- and ectoparasiticidal insecticidal, acaricidal and nematocidal agents
ATE148611T1 (de) *	1989-12-15	1997-02-15	American Cyanamid Co	''pour-on''-formulierungen zur bekämpfung von internen und externen parasiten bei homoöthermen tieren
US6514951B1 (en)	1989-12-15	2003-02-04	American Cyanamid Company	Pour-on formulations effective for the control of internal and external parasites of homothermic animals
GB9024926D0 (en) *	1990-11-16	1991-01-02	Beecham Group Plc	Novel treatment
GB9024927D0 (en) *	1990-11-16	1991-01-02	Beecham Group Plc	Novel treatment
GB9205007D0 (en) *	1992-03-07	1992-04-22	Pfizer Ltd	Antiparasitic agents
SK1282004A3 (en)	2001-09-17	2004-08-03	Lilly Co Eli	Pesticidal formulations
US6979409B2 (en)	2003-02-06	2005-12-27	Magnequench, Inc.	Highly quenchable Fe-based rare earth materials for ferrite replacement
AU2006203349B2 (en) *	2006-05-08	2008-01-31	Wyeth	Process
AU2006100664B4 (en) *	2006-05-08	2006-09-14	Wyeth	Oxidation process and use thereof
AU2006203345B1 (en) *	2006-07-06	2007-12-13	Wyeth	Biocatalytic oxidation process and use thereof
WO2012028556A1 (en)	2010-08-31	2012-03-08	Bayer Animal Health Gmbh	Macrocyclic lactones and their use and their combinations with other active substances
DE102010064245A1 (de)	2010-12-28	2012-06-28	Bayer Animal Health Gmbh	Makrocylischen Lactone und deren Verwendung und deren Kombinationen mit anderen Wirkstoffen
ITUB20153652A1 (it)	2015-09-16	2017-03-16	Fatro Spa	Microsfere contenenti lattoni macrociclici antielminitici

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4289760A (en) *	1980-05-02	1981-09-15	Merck & Co., Inc.	23-Keto derivatives of C-076 compounds
DE3519834C2 (de) *	1984-06-05	1993-12-16	American Cyanamid Co	Neue antibiotische Wirkstoffe, Verfahren zu ihrer Gewinnung und ihre Anwendung zur Bekämpfung von Infektionen bei Tieren und Pflanzen
GB2166436B (en) *	1984-09-14	1989-05-24	Glaxo Group Ltd	Antibiotic compounds and their preparation
ES8802229A1 (es) *	1985-04-30	1988-04-16	Glaxo Group Ltd	Un procedimiento para preparar nuevos derivados lactonicos macrociclicos.
DE3650265T2 (de) *	1985-09-13	1995-07-27	American Cyanamid Co	Makrolide Antibiotika und Verfahren zu deren Herstellung.
EP0238259B1 (en) *	1986-03-12	1993-09-29	American Cyanamid Company	Macrolide compounds
CA1296329C (en) *	1986-06-06	1992-02-25	Derek R. Sutherland	Macrolide compounds

1987
- 1987-09-03 ES ES87112854T patent/ES2058082T3/es not_active Expired - Lifetime
- 1987-09-03 EP EP87112854A patent/EP0259779B1/en not_active Expired - Lifetime
- 1987-09-03 AT AT87112854T patent/ATE109783T1/de not_active IP Right Cessation
- 1987-09-03 DE DE3750355T patent/DE3750355T2/de not_active Expired - Lifetime
- 1987-09-06 IL IL83796A patent/IL83796A0/xx unknown
- 1987-09-08 NZ NZ221714A patent/NZ221714A/xx unknown
- 1987-09-10 PT PT85674A patent/PT85674B/pt unknown
- 1987-09-10 CA CA000546561A patent/CA1301164C/en not_active Expired - Lifetime
- 1987-09-11 IE IE243887A patent/IE65147B1/en not_active IP Right Cessation
- 1987-09-11 BR BR8704738A patent/BR8704738A/pt not_active IP Right Cessation
- 1987-09-11 KR KR1019870010145A patent/KR960004941B1/ko not_active Expired - Fee Related
- 1987-09-11 DK DK475587A patent/DK170822B1/da not_active IP Right Cessation
- 1987-09-11 AR AR87308706A patent/AR246267A1/es active
- 1987-09-11 ZA ZA876832A patent/ZA876832B/xx unknown
- 1987-09-11 HU HU874048A patent/HU203239B/hu unknown
- 1987-09-11 AU AU78281/87A patent/AU604749B2/en not_active Expired
- 1987-09-12 JP JP62229437A patent/JP2654028B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
EP0259779B1 (en)	1994-08-10
JP2654028B2 (ja)	1997-09-17
IE872438L (en)	1988-03-12
AU604749B2 (en)	1991-01-03
AR246267A1 (es)	1994-07-29
IL83796A0 (en)	1988-02-29
DE3750355D1 (de)	1994-09-15
DK475587D0 (da)	1987-09-11
DE3750355T2 (de)	1995-04-06
BR8704738A (pt)	1988-05-03
KR960004941B1 (ko)	1996-04-18
JPS63119486A (ja)	1988-05-24
HU203239B (en)	1991-06-28
CA1301164C (en)	1992-05-19
DK475587A (da)	1988-03-13
HK1000010A1 (en)	1997-10-03
KR880003951A (ko)	1988-06-01
PT85674B (pt)	1990-05-31
NZ221714A (en)	1990-10-26
ES2058082T3 (es)	1994-11-01
HUT45534A (en)	1988-07-28
AU7828187A (en)	1988-03-31
ZA876832B (en)	1988-03-15
EP0259779A1 (en)	1988-03-16
ATE109783T1 (de)	1994-08-15
IE65147B1 (en)	1995-10-04
PT85674A (en)	1987-10-01

Publication	Publication Date	Title
DK170822B1 (da)	1996-01-29	23-Oxo- og -iminoderivater af LL-F28249-forbindel ser, deres anvendelse ved fremgangsmåder til bekæmpelse af skadelige insekter og plantenematoder samt midler indeholdende dem til bekæmpelse af insekter og af endo- og/eller ectoparasitter hos varmblodede dyr
US4916154A (en)	1990-04-10	23-Imino derivatives of LL-F28249 compounds
DK167219B1 (da)	1993-09-20	Delta22-derivater af ll-f28249-forbindelser samt anvendelse deraf
DE3885346T2 (de)	1994-05-19	23-Oxo (Keto) und 23-Imino-Derivate von Mono- und Diepoxy LL-F28249 Verbindungen.
US4849446A (en)	1989-07-18	23-imino derivatives of 23-keto compounds
DE3787942T2 (de)	1994-05-11	Mono- und Diacylderivate von LL-F28249-Verbindungen.
EP0293548B1 (en)	1994-07-27	Mono- and diepoxide derivatives of LL-F28249 compounds
DE3782481T2 (de)	1993-05-19	23-deoxy-derivate von ll-f28249-verbindungen.
US4857544A (en)	1989-08-15	27-Halo derivatives of LL-F28249 compounds
US4956479A (en)	1990-09-11	23-deoxy-27-chloro derivatives of LL-F28249 compounds
EP0260537A1 (en)	1988-03-23	13-Deoxy-23-oxo(keto) and 23-imino derivatives of 13-deoxy C-076-aglycone compounds
US5019589A (en)	1991-05-28	Δ23 -LL-F28249 compounds
CA1291129C (en)	1991-10-22	Mono- and diepoxide derivatives of delta__-ll-f28249 compounds
CA1300617C (en)	1992-05-12	Mono- and diepoxide derivatives of 23-deoxy-ll-f28249 compounds
US4877888A (en)	1989-10-31	13-deoxy-23-imino derivatives of 13-deoxy C-076-aglycone compounds
HK1000010B (en)	1997-10-03	23-oxo (keto) and 23-imino derivatives of ll-f28249 compounds

Legal Events

Date	Code	Title	Description
1996-01-29	B1	Patent granted (law 1993)
2007-10-01	PUP	Patent expired